Compositions comprising organic and organometallic compounds, and their applications in organic electroluminescence, light emission, display, and illumination devices

ABSTRACT

An object of the present invention is to provide an organic electroluminescence device having excellent light emission efficiency and durability, in particular, durability when driving at a high temperature. Provided is an organic electroluminescence device including on a substrate a pair of electrodes, and at least one layer of an organic layer including a light emitting layer containing a light emitting material disposed between the electrodes, wherein the light emitting layer includes at least each one of specific indolocarbazole derivatives and specific condensed ring metal complexes.

TECHNICAL FIELD

The present invention relates to a luminescence device that may convertelectric energy into light to emit light, and particularly, to anorganic electroluminescence device (referred to as a luminescencedevice, an EL device or device).

BACKGROUND ART

Organic electroluminescence (EL) devices are capable of obtaining alight emission with high luminance intensity at low voltage, and thus,have gained attention as a promising display device. An importantcharacteristic value of the organic electroluminescence device iselectric power consumption. The electric power consumption is expressedas the product of voltage and electric current, and the lower thevoltage is required to obtain a desired brightness and the smaller valuethe electric current becomes, the lower the power consumption of thedevice may be made.

As one attempt to lower the value of electric current that flows throughthe device, a luminescence device utilizing light emission from anortho-metalated iridium complex (Ir(ppy)₃: tris-ortho-metalated complexof Iridium(III) with 2-phenylpyridine) has been reported (see, forexample, Patent Documents 1 to 3). The phosphorescent luminescencedevice described therein is greatly enhanced in the external quantumefficiency as compared with singlet luminescence devices of the relatedart, and thus, succeeded in lowering the value of electric current.

As described above, although the iridium complex is used as a lightemission material for implementing light emission efficiency, thesolubility is generally poor, and thus, there was a case where theservice life of the device was shortened due to aggregation orassociation of the complex. In particular, when the complex has acondensed ring structure such as a quinoline ring and an isoquinolinering in the ligand, it is considered that the degree of freedom ofmolecular motion is decreased, and thus, the complex is easilyaggregated. In order to suppress aggregation or association of thecomplex, an attempt to increase the solubility has been made byintroducing, for example, a specific substituent (Patent Documents 4 and5), but the effects thereof were not sufficient.

Meanwhile, devices using a compound which has an indolocarbazolestructure as a host material for the purpose of improving light emissionefficiency and durability of a phosphorescent luminescence device(Patent Documents 6 and 7) have been reported, but more improvements aredemanded from the viewpoint of durability and light emission efficiency.

Further, since indolocarbazole also has an extended p-conjugated plane,and has a small degree of freedom of molecular motion, it is consideredthat association and aggregation is easily generated.

In addition, in the manufacture of an organic electroluminescencedevice, a method for forming a thin film which is an organic layerdisposed between a pair of electrodes includes a deposition method suchas vacuum deposition, and a wet method such as a spin coating method, aprinting method and an inkjet method.

Among them, if a wet method is used, it is also possible to usepolymeric organic compounds, for which it is difficult to form a film indry processes such as vapor deposition, and when a wet method is used ina flexible display and the like, the method is appropriate from theviewpoint of durability such as flex resistance, film strength and thelike, and when the device is manufactured to have a large area, themethod is particularly preferable.

However, organic electroluminescence devices obtained by a wet methodwere problematic in that the devices have low light emission efficiencyor device durability.

RELATED ART Patent Document

Patent Document 1: US Patent Application Publication No. 2008/0297033

Patent Document 2: Japanese Patent Application Laid-Open No. 2008-297382

Patent Document 3: Japanese Patent Application Laid-Open No. 2008-137994

Patent Document 4: International Publication No. WO08/109,824

Patent Document 5: International Publication No. WO09/073,245

Patent Document 6: International Publication No. WO07/063,796

Patent Document 7: International Publication No. WO07/063,754

DISCLOSURE OF INVENTION Problems to be Solved by the Invention

An object of the present invention is to provide an organicelectroluminescence device having excellent light emission efficiencyand durability (in particular, durability when driving at a hightemperature).

Means for Solving the Problems

The above object is solved by the following means.

[1] An organic electroluminescence device, comprising on a substrate:

a pair of electrodes; and

at least one layer of an organic layer including a light emitting layercontaining a light emitting material disposed between the electrodes,

wherein the light emitting layer contains at least each one of acompound represented by the following Formula (3) and a compoundrepresented by the following Formula (D-1):Z³

Y³)_(n) ₃   (3)

wherein Z³ represents benzene, pyridine, triazine, pyrimidine, biphenyl,phenylpyridine, bipyridine, a silicon atom or a carbon atom, and may befurther substituted by at least one group selected from an alkyl group,an aryl group, a silyl group, a cyano group, a fluorine atom and acombination thereof;

Y³ represents a group represented by the following Formula (3a-1) or(3a-2); and

n³ represents an integer of 1 to 4:

in Formulas (3a-1) and (3a-2), the ring A represents an aromatic ring ora heterocyclic ring, represented by Formula (3b), which is condensedwith an adjacent ring;

the ring B represents a heterocyclic ring represented by Formula (3c),which is condensed with an adjacent ring;

X³ represents C—R″ in which R″ represents a hydrogen atom or asubstituent, or a nitrogen atom;

each of R₃₄ and R₃₁₁ independently represents a benzene ring, anaphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring,and these rings may be further substituted by at least one groupselected from a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group and afluorine atom;

R₃₃ represents a hydrogen atom;

each of R₃₁ and R₃₂ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup, if possible; and

* represents a bond for linking to Z³:

in Formula (D-1), M represents iridium;

each of R₃ to R₆ independently represents a hydrogen atom, an alkylgroup or an aryl group;

R₃′ represents a hydrogen atom, an alkyl group or an aryl group;

the ring Q represents a pyridine ring, a quinoline ring or anisoquinoline ring, which is coordinated to iridium, and may be furthersubstituted by an alkyl group or an aryl group;

R₅ represents an aryl group or a heteroaryl group when the ring Q is apyridine ring, and the aryl group or the heteroaryl group may be furthersubstituted by an alkyl group;

R₃′ and R₆ may be linked to each other by a linking group selected from—CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —O—CR₂—, —NR—CR₂— and —N═CR— toform a ring;

each R independently represents a hydrogen atom, an alkyl group, analkenyl group, an alkynyl group, an aryl group or a heteroaryl group,and may further have a substituent selected from a halogen atom, —R′,—OR′, —N(R)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)_(N)(R′)₂, —CN, —NO₂, —SO₂,—SOR′, —SO₂R′ and —SO₃R′;

each R′ independently represents a hydrogen atom, an alkyl group, aperhaloalkyl group, an alkenyl group, an alkynyl group, an aryl group ora heteroaryl group;

(X—Y) represents a ligand represented by any one of the followingFormula (1-1), (1-4) or (1-15);

m represents an integer of 1 to 3; and

n represents an integer of 0 to 2, provided that m+n is 3:

in Formulas (1-1), (1-4) and (1-15), each of Rx, Ry and Rz independentlyrepresents a hydrogen atom, an alkyl group, a perfluoroalkyl group, ahalogen atom or an aryl group.

[2] The organic electroluminescence device as described in [1] above,

wherein the compound represented by Formula (3) is represented by thefollowing Formula (1):

wherein the ring A represents an aromatic ring or a heterocyclic ring,represented by Formula (1a), which is condensed with an adjacent ring;

the ring B represents a heterocyclic ring represented by Formula (1b),which is condensed with an adjacent ring;

X¹ represents C—R″ in which R″ represents a hydrogen atom or asubstituent, or a nitrogen atom;

each of R₁₁ and R₁₅ independently represents a benzene ring, anaphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring,and these rings may be further substituted by at least one groupselected from a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group and afluorine atom;

R₁₄ represents a hydrogen atom; and

each of R₁₂ and R₁₃ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup.

[3] The organic electroluminescence device as described in [2] above,

wherein the compound represented by Formula (1) is represented by thefollowing Formula (15):

wherein X₁₅₁ to X₁₅₃ represent a nitrogen atom or C—R₁₅₃;

R₁₅₃ represents a hydrogen atom, a methyl group, an isobutyl group, at-butyl group, a neopentyl group, a phenyl group, a naphthyl group, acyano group or a fluorine atom;

each of R₁₅₁ and R₁₅₂ independently represents a hydrogen atom, a methylgroup, an isobutyl group, a t-butyl group, a neopcntyl group, a phenylgroup, a naphthyl group, a cyano group or a fluorine atom; and

Y¹⁵ represents a group represented by any one of the following Formulas(15a) to (15c):

wherein R₁₅₅ represents a hydrogen atom;

each of R₁₅₄ and R₁₅₆ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup; and

R₁₅₇ represents a benzene ring, a naphthalene ring, a pyridine ring, atriazine ring or a pyrimidine ring, and these rings may be furthersubstituted by at least one group selected from a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom.

[4] The organic electroluminescence device as described in [3] above,

wherein the compound represented by Formula (15) is represented by thefollowing Formula (16):

wherein X₁₆₁ to X₁₆₃ represent a nitrogen atom or C—H, and each of R₁₆₁and R₁₆₂ independently represents a hydrogen atom, a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group or a fluorine atom; and

Y¹⁶ represents a group represented by any one of the Formulas (15a) to(15c).

[5] The organic electroluminescence device as described in [4] above,

wherein the compound represented by Formula (16) is represented by thefollowing Formula (17):

wherein each of R₁₇₁ and R₁₇₂ independently represents a hydrogen atom,a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group or a fluorine atom; and

Y¹⁷ represents a group represented by any one of the Formulas (15a) to(15c).

[6] The organic electroluminescence device as described in [4] above,

wherein the compound represented by Formula (16) is represented by thefollowing Formula (18):

wherein each of R₁₈₁ and R₁₈₂ independently represents a hydrogen atom,a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group or a fluorine atom; and

Y¹⁸ represents a group represented by any one of the Formulas (15a) to(15c).

[7] The organic electroluminescence device as described in [1] above,

wherein the compound represented by Formula (3) is represented by thefollowing Formula (5):

wherein each of R₅₁ to R₅₆ independently represents a hydrogen atom, amethyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group, a fluorine atom or agroup represented by any one of the following Formula (10), (10-2) or(10-3), provided that each of at least two of R₅₁ to R₅₆ isindependently a group represented by any one of the following Formula(10), (10-2) or (10-3):

wherein R₁₀₂ represents a hydrogen atom;

each of R₁₀₁ and R₁₀₃ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup; and

R₁₀₄ represents a benzene ring, a naphthalene ring, a pyridine ring, atriazine ring or a pyrimidine ring, and these rings may be furthersubstituted by at least one group selected from a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom.

[8] The organic electroluminescence device as described in [1] above,

wherein the compound represented by Formula (3) is represented by thefollowing Formula (6):

wherein each of R₆₁ to R₆₁₀ independently represents a hydrogen atom, amethyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group, a fluorine atom or agroup represented by any one of the following Formula (10), (10-2) or(10-3), provided that each of at least two of R₆₁ to R₆₁₀ isindependently a group represented by any one of the following Formula(10), (10-2) or (10-3):

wherein R₁₀₂ represents a hydrogen atom;

each of R₁₀₁ and R₁₀₃ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup; and

R₁₀₄ represents a benzene ring, a naphthalene ring, a pyridine ring, atriazine ring or a pyrimidine ring, and these rings may be furthersubstituted by at least one group selected from a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom.

[9] The organic electroluminescence device as described in [8] above,

wherein the compound represented by Formula (6) is represented by thefollowing Formula (7):

wherein each of R₇₁ to R₇₈ independently represents a hydrogen atom, amethyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group, a fluorine atom or agroup represented by any one of the following Formula (10), (10-2) or(10-3); and

each of Y₇₁ and Y₇₂ is independently a group represented by any one ofthe following Formula (10), (10-2) or (10-3):

wherein R₁₀₂ represents a hydrogen atom;

each of R₁₀₁ and R₁₀₃ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup; and

R₁₀₄ represents a benzene ring, a naphthalene ring, a pyridine ring, atriazine ring or a pyrimidine ring, and these rings may be furthersubstituted by at least one group selected from a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom.

[10] The organic electroluminescence device as described in [8] above,

wherein the compound represented by Formula (6) is represented by thefollowing Formula (8):

wherein each of R₈₁ to R₈₈ independently represents a hydrogen atom, amethyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group, a fluorine atom or agroup represented by any one of the following Formula (10), (10-2) or(10-3); and

each of Y₈₁ and Y₈₂ is independently a group represented by any one ofthe following Formula (10), (10-2) or (10-3):

wherein R₁₀₂ represents a hydrogen atom;

each of R₁₀₁ and R₁₀₃ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup; and

R₁₀₄ represents a benzene ring, a naphthalene ring, a pyridine ring, atriazine ring or a pyrimidine ring, and these rings may be furthersubstituted by at least one group selected from a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom.

[11] The organic electroluminescence device as described in [1] above,

wherein the compound represented by Formula (3) is represented by thefollowing Formula (9):

wherein each of R₉₁ to R₉₁₀ independently represents a hydrogen atom, amethyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group, a fluorine atom or agroup represented by any one of the following Formula (10), (10-2) or(10-3), provided that each of at least two of R₉₁ to R₉₁₀ isindependently a group represented by any one of the following Formula(10), (10-2) or (10-3); and

L₁ represents a silicon atom or a carbon atom, and the silicon atom orthe carbon atom may be further substituted by at least one groupselected from an alkyl group and an aryl group:

wherein R₁₀₂ represents a hydrogen atom;

each of R₁₀₁ and R₁₀₃ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup; and

R₁₀₄ represents a benzene ring, a naphthalene ring, a pyridine ring, atriazine ring or a pyrimidine ring, and these rings may be furthersubstituted by at least one group selected from a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom.

[12] The organic electroluminescence device as described in [1] above,

wherein the compound represented by Formula (3) is represented by thefollowing Formula (11):

wherein each of R₁₁₁ to R₁₁₆ independently represents a hydrogen atom, amethyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group, a fluorine atom or agroup represented by any one of the following Formula (10), (10-2) or(10-3), provided that at least one of R₁₁₁ to R₁₁₅ is a grouprepresented by any one of the following Formula (10), (10-2) or (10-3);and

m represents an integer of 1 to 4:

wherein R₁₀₂ represents a hydrogen atom;

each of R₁₀₁ and R₁₀₃ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup; and

R₁₀₄ represents a benzene ring, a naphthalene ring, a pyridine ring, atriazine ring or a pyrimidine ring, and these rings may be furthersubstituted by at least one group selected from a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom.

[13] The organic electroluminescence device as described in [1] above,

wherein the compound represented by Formula (3) is represented by thefollowing Formula (12):

wherein each of R₁₂₁ to R₁₂₆ independently represents a hydrogen atom, amethyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group, a fluorine atom or agroup represented by any one of the following Formula (10), (10-2) or(10-3), provided that at least one of R₁₂₁ to R₁₂₅ is independently agroup represented by any one of the following Formula (10), (10-2) or(10-3); and

m represents an integer of 1 to 4:

wherein R₁₀₂ represents a hydrogen atom;

each of R₁₀₁ and R₁₀₃ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup; and

R₁₀₄ represents a benzene ring, a naphthalene ring, a pyridine ring, atriazine ring or a pyrimidine ring, and these rings may be furthersubstituted by at least one group selected from a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom.

[14] The organic electroluminescence device as described in [1] above,

wherein the compound represented by Formula (3) is represented by thefollowing Formula (13):

wherein R₁₃₂ represents a hydrogen atom;

each of R₁₃₁ and R₁₃₃ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup;

each of R₁₃₄ and R₁₃₅ independently represents a benzene ring, anaphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring,and these rings may be further substituted by at least one groupselected from a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group and afluorine atom;

R₁₃₆ represents a hydrogen atom, a methyl group, an isobutyl group, at-butyl group, a neopentyl group, a phenyl group, a naphthyl group, acyano group or a fluorine atom;

m represents an integer of 1 to 4; and

a silicon linking group is substituted to a carbon atom as one of R₁₃₁.

[15] The organic electroluminescence device as described in [1] above,

wherein the compound represented by Formula (3) is represented by thefollowing Formula (14):

wherein R₁₄₂ represents a hydrogen atom;

each of R₁₄₁ and R₁₄₃ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup;

each of R₁₄₄ and R₁₄₅ independently represents a benzene ring, anaphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring,and these rings may be further substituted by at least one groupselected from a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group and afluorine atom;

a carbon linking group is substituted to a carbon atom as one of R₁₄₁;

R₁₄₆ represents a hydrogen atom, a methyl group, an isobutyl group, at-butyl group, a neopentyl group, a phenyl group, a naphthyl group, acyano group or a fluorine atom; and

m represents an integer of 1 to 4.

[16] The organic electroluminescence device as described in any one of[1] to [15] above,

wherein the compound represented by Formula (D-1) is a compoundrepresented by the following Formula (D-2):

in Formula (D-2), M represents iridium;

each of R₃ to R₆ independently represents a hydrogen atom, an alkylgroup or an aryl group;

R₃′ to R₈′ represent a hydrogen atom, an alkyl group or an aryl group;

R₃′ and R₆ may be linked to each other by a linking group selected from—CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —O—CR₂—, —NR—CR₂— and —N═CR— toform a ring;

each R independently represents a hydrogen atom, an alkyl group, analkenyl group, an alkynyl group, an aryl group or a heteroaryl group,and may further have a substituent selected from a halogen atom, —R′,—OR′, —N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)_(N)(R′)₂, —CN, —NO₂, —SO₂,—SOR′, —SO₂R′ and —SO₃R′;

each R′ independently represents a hydrogen atom, an alkyl group, aperhaloalkyl group, an alkenyl group, an alkynyl group, an aryl group ora heteroaryl group;

(X—Y) represents a ligand represented by any one of Formula (1-1), (1-4)or (1-15);

m represents an integer of 1 to 3; and

n represents an integer of 0 to 2, provided that m+n is 3.

[17] The organic electroluminescence device as described in any one of[1] to [15] above,

wherein the compound represented by Formula (D-1) is a compoundrepresented by the following Formula (D-3):

in Formula (D-3), M represents iridium;

each of R₃ to R₆ independently represents a hydrogen atom, an alkylgroup or an aryl group;

each of R₃′ to R₈′ independently represents a hydrogen atom, an alkylgroup or an aryl group;

R₃′ and R₆ may be linked to each other by a linking group selected from—CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —O—CR₂—, —NR—CR₂— and —N═CR— toform a ring;

each R independently represents a hydrogen atom, an alkyl group, analkenyl group, an alkynyl group, an aryl group or a heteroaryl group,and may further have a substituent selected from a halogen atom, —R′,—OR′, —N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)₂, —CN, —NO₂, —SO₂,—SOR′, —SO₂R′ and —SO₃R′;

each R′ independently represents a hydrogen atom, an alkyl group, aperhaloalkyl group, an alkenyl group, an alkynyl group, an aryl group ora heteroaryl group;

(X—Y) represents a ligand represented by any one of Formula (1-1), (1-4)or (1-15);

m represents an integer of 1 to 3; and

n represents an integer of 0 to 2, provided that m+n is 3.

[18] The organic electroluminescence device as described in any one of[1] to [15] above,

wherein the compound represented by Formula (D-1) is a compoundrepresented by the following Formula (D-4):

in Formula (D-4), M represents iridium;

each of R₃ to R₁₀ independently represents a hydrogen atom, an alkylgroup or an aryl group;

each of R₃′ to R₆′ independently represents a hydrogen atom, an alkylgroup or an aryl group;

R₃′ and R₁₀ may be linked to each other by a linking group selected from—CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —O—CR₂—, —NR—CR₂— and —N═CR— toform a ring;

each R independently represents a hydrogen atom, an alkyl group, analkenyl group, an alkynyl group, an aryl group or a heteroaryl group,and may further have a substituent selected from a halogen atom, —R′,—OR′, —N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)₂, —CN, —NO₂, —SO₂,—SOR′, —SO₂R′ and —SO₃R′;

each R′ independently represents a hydrogen atom, an alkyl group, aperhaloalkyl group, an alkenyl group, an alkynyl group, an aryl group ora heteroaryl group;

(X—Y) represents a ligand represented by any one of Formula (1-1), (1-4)or (1-15);

m represents an integer of 1 to 3; and

n represents an integer of 0 to 2, provided that m+n is 3.

[19] The organic electroluminescence device as described in any one of[1] to [18] above,

wherein the light emitting layer containing at least each one of thecompound represented by Formula (3) and the compound represented byFormula (D-1) is formed by a wet process.

[20] A composition, comprising:

at least each one of a compound represented by the following Formula (3)and a compound represented by the following Formula (D-1):Z³

Y³)_(n) ₃   (3)

wherein Z³ represents benzene, pyridine, triazine, pyrimidine, biphenyl,phenylpyridine, bipyridine, a silicon atom or a carbon atom, and may befurther substituted by at least one group selected from an alkyl group,an aryl group, a silyl group, a cyano group, a fluorine atom and acombination thereof;

Y³ represents a group represented by the following Formula (3a-1) or(3a-2); and

n³ represents an integer of 1 to 4:

in Formulas (3a-1) and (3a-2), the ring A represents an aromatic ring ora heterocyclic ring, represented by Formula (3b), which is condensedwith an adjacent ring;

the ring B represents a heterocyclic ring represented by Formula (3c),which is condensed with an adjacent ring;

X³ represents C—R″ in which R″ represents a hydrogen atom or asubstituent, or a nitrogen atom;

each of R₃₄ and R₃₁₁ independently represents a benzene ring, anaphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring,and these rings may be further substituted by at least one groupselected from a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group and afluorine atom;

R₃₃ represents a hydrogen atom;

each of R₃₁ and R₃₂ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup, if possible; and

* represents a bond for linking to Z³:

in Formula (D-1), M represents iridium;

each of R₃ to R₆ independently represents a hydrogen atom, an alkylgroup or an aryl group;

R₃′ represents a hydrogen atom, an alkyl group or an aryl group;

the ring Q represents a pyridine ring, a quinoline ring or anisoquinoline ring, which is coordinated to iridium, and may be furthersubstituted by an alkyl group or an aryl group;

R₅ represents an aryl group or a heteroaryl group when the ring Q is apyridine ring, and the aryl group or the heteroaryl group may be furthersubstituted by an alkyl group;

R₃′ and R₆ may be linked to each other by a linking group selected from—CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —O—CR₂—, —NR—CR₂— and —N═CR— toform a ring;

each R independently represents a hydrogen atom, an alkyl group, analkenyl group, an alkynyl group, an aryl group or a heteroaryl group,and may further have a substituent selected from a halogen atom, —R′,—OR′, —N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)₂, —CN, —NO₂, —SO₂,—SOR′, —SO₂R′ and —SO₃R′;

each R′ independently represents a hydrogen atom, an alkyl group, aperhaloalkyl group, an alkenyl group, an alkynyl group, an aryl group ora heteroaryl group;

(X—Y) represents a ligand represented by any one of the followingFormula (1-1), (I-4) or (1-15);

m represents an integer of 1 to 3; and

n represents an integer of 0 to 2, provided that m+n is 3:

in Formulas (1-1), (1-4) and (1-15), each of Rx, Ry and Rz independentlyrepresents a hydrogen atom, an alkyl group, a perfluoroalkyl group, ahalogen atom or an aryl group.

[21] A light emitting layer, comprising:

at least each one of a compound represented by the following Formula (3)and a compound represented by the following Formula (D-1):Z³

Y³)_(n) ₃   (3)

wherein Z³ represents benzene, pyridine, triazine, pyrimidine, biphenyl,phenylpyridine, bipyridine, a silicon atom or a carbon atom, and may befurther substituted by at least one group selected from an alkyl group,an aryl group, a silyl group, a cyano group, a fluorine atom and acombination thereof;

Y³ represents a group represented by the following Formula (3a-1) or(3a-2); and

n³ represents an integer of 1 to 4:

in Formulas (3a-1) and (3a-2), the ring A represents an aromatic ring ora heterocyclic ring represented by Formula (3b), which is condensed withan adjacent ring;

the ring B represents a heterocyclic ring represented by Formula (3c),which is condensed with an adjacent ring;

X³ represents C—R″ in which R″ represents a hydrogen atom or asubstituent, or a nitrogen atom;

each of R₃₄ and R₃₁₁ independently represents a benzene ring, anaphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring,and these rings may be further substituted by at least one groupselected from a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group and afluorine atom;

R₃₃ represents a hydrogen atom;

each of R₃₁ and R₃₂ independently represents a hydrogen atom, an alkylgroup, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted by atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup, if possible; and

* represents a bond for linking to Z³:

in Formula (D-1), M represents iridium;

each of R₃ to R₆ independently represents a hydrogen atom, an alkylgroup or an aryl group;

R₃′ represents a hydrogen atom, an alkyl group or an aryl group;

the ring Q represents a pyridine ring, a quinoline ring or anisoquinoline ring, which is coordinated to iridium, and may be furthersubstituted by an alkyl group or an aryl group;

R₅ represents an aryl group or a heteroaryl group when the ring Q is apyridine ring, and the aryl group or the heteroaryl group may be furthersubstituted by an alkyl group;

R₃′ and R₆ may be linked to each other by a linking group selected from—CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —O—CR₂—, —NR—CR₂— and —N═CR— toform a ring;

each R independently represents a hydrogen atom, an alkyl group, analkenyl group, an alkynyl group, an aryl group or a heteroaryl group,and may further have a substituent selected from a halogen atom, —R′,—OR′, —N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)₂, —CN, —NO₂, —SO₂,—SOR′, —SO₂R′ and —SO₃R′;

each R′ independently represents a hydrogen atom, an alkyl group, aperhaloalkyl group, an alkenyl group, an alkynyl group, an aryl group ora heteroaryl group;

(X—Y) represents a ligand represented by any one of the followingFormula (1-1), (I-4) or (1-15);

m represents an integer of 1 to 3; and

n represents an integer of 0 to 2, provided that m+n is 3:

in Formulas (1-1), (1-4) and (1-15), each of Rx, Ry and Rz independentlyrepresents a hydrogen atom, an alkyl group, a perfluoroalkyl group, ahalogen atom or an aryl group.

[22] A light emission apparatus using the organic electroluminescencedevice as described in any one of [1] to [19] above.

[23] A display apparatus using the organic electroluminescence device asdescribed in any one of [1] to [19] above.

[24] An illumination apparatus using the organic electroluminescencedevice as described in any one of [1] to [19] above.

Further, the present invention preferably has the followingconfiguration.

<1>

An organic electroluminescence device, comprising on a substrate:

a pair of electrodes; and

at least one layer of an organic layer including a light emitting layercontaining a light emitting material disposed between the electrodes,

wherein the light emitting layer contains at least each one of acompound represented by the following Formula (7), (8) or (11) and acompound represented by the following Formula (D-4), (D-2) or (D-3):

wherein R₇₁ to R₇₈ represent a hydrogen atom; and

each of Y₇₁ and Y₇₂ independently represents a group represented by thefollowing Formula (10):

wherein R₈₁ to R₈₈ represent a hydrogen atom; and

each of Y₈₁ and Y₈₂ independently represents a group represented by thefollowing Formula (10):

wherein R₁₁₃ represents a group represented by the following Formula(10);

R₁₁₁, R₁₁₂, R₁₁₄ and R₁₁₅ represent a hydrogen atom;

R₁₁₆ represents a hydrogen atom, an alkyl group or an aromatichydrocarbon ring group; and

m represents 2:

wherein R₁₀₁ to R₁₀₃ represent a hydrogen atom; and

R₁₀₄ represents a benzene ring, a biphenyl ring or a pyridine ring, andthese rings may be further substituted with an alkyl group having 1 to 6carbon atoms, a phenyl group or a pyridyl group:

in Formula (D-4), M represents iridium;

each of R₃ to R₁₀ independently represents a hydrogen atom, an alkylgroup or an aryl group;

each of R₃′ to R₆′ independently represents a hydrogen atom, an alkylgroup or an aryl group;

(X—Y) represents a ligand of phenylpyridine, picolinic acid oracetylacetone, and the phenylpyridine may be substituted with an alkylgroup;

m represents 1 to 3; and

n represents 0 to 2, provided that m+n is 3:

in Formula (D-2), M represents iridium;

each of R₃ to R₆ independently represents a hydrogen atom, an alkylgroup or an aryl group;

each of R₃′ to R₈′ independently represents a hydrogen atom, an alkylgroup or an aryl group;

(X—Y) represents a ligand of phenylpyridine, picolinic acid oracetylacetone, and the phenylpyridine may be substituted with an alkylgroup;

m represents 1 to 3; and

n represents 0 to 2, provided that m+n is 3:

in Formula (D-3), M represents iridium;

each of R₃ to R₆ independently represents a hydrogen atom, an alkylgroup or an aryl group;

each of R₃′ to R₃′ independently represents a hydrogen atom, an alkylgroup or an aryl group;

(X—Y) represents a ligand of phenylpyridine, picolinic acid oracetylacetone, and the phenylpyridine may be substituted with an alkylgroup;

m represents 1 to 3; and

n represents 0 to 2, provided that m+n is 3.

<2>

The organic electroluminescence device as described in <1>,

wherein R₁₀₄ in Formula (10) represents a benzene ring, a biphenyl ringor a pyridine ring.

<3>

The organic electroluminescence device as described in <I>,

wherein R₁₀₄ in Formula (10) represents a benzene ring.

<4>

The organic electroluminescence device as described in any one of <1> to<3>,

wherein R₁₁₆ in Formula (11) represents an alkyl group or an aromatichydrocarbon ring group.

<5>

The organic electroluminescence device as described in any one of <1> to<4>, wherein each of, R₃ to R₆ and R₃′ to R₈′ in Formula (D-2), R₃ to R₆and R₃′ to R₈′ in Formula (D-3), or R₃ to R₁₀ and R₃′ to R₆′ in Formula(D-4) independently represents a hydrogen atom or an alkyl group.

<6>

The organic electroluminescence device as described in any one of <I> to<5>, wherein a light emitting layer containing at least each one of thecompound represented by Formula (7), (8) or (11) and the compoundrepresented by Formula (D-4), (D-2) or (D-3) is formed by a wet process.

<7>

A composition, containing:

at least each one of a compound represented by the following Formula(7), (8) or (11) and a compound represented by the following Formula(D-4), (D-2) or (D-3):

wherein R₇₁ to R₇₈ represent a hydrogen atom; and

each of Y₇₁ and Y₇₂ independently represents a group represented by thefollowing Formula (10):

wherein R₈₁ to R₈₈ represent a hydrogen atom; and

each of Y₈₁ and Y₈₂ independently represents a group represented by thefollowing Formula (10):

wherein R₁₁₃ represents a group represented by the following Formula(10);

R₁₁₁, R₁₁₂, R₁₁₄ and R₁₁₅ represent a hydrogen atom;

R₁₁₆ represents a hydrogen atom, an alkyl group or an aromatichydrocarbon ring group; and

m represents 2:

wherein R₁₀₁ to R₁₀₃ represent a hydrogen atom; and R₁₀₄ represents abenzene ring, a biphenyl ring or a pyridine ring, and these rings may befurther substituted with an alkyl group having 1 to 6 carbon atoms, aphenyl group or a pyridyl group:

in Formula (D-4), M represents iridium;

each of R₃ to R₁₀ independently represents a hydrogen atom, an alkylgroup or an aryl group;

each of R₃′ to R₆′ independently represents a hydrogen atom, an alkylgroup or an aryl group;

(X—Y) represents a ligand of phenylpyridine, picolinic acid oracetylacetone, and the phenylpyridine may be substituted with an alkylgroup;

m represents 1 to 3; and

n represents 0 to 2, provided that m+n is 3:

in Formula (D-2), M represents iridium;

each of R₃ to R₆ independently represents a hydrogen atom, an alkylgroup or an aryl group;

each of R₃′ to R₈′ independently represents a hydrogen atom, an alkylgroup or an aryl group;

(X—Y) represents a ligand of phenylpyridine, picolinic acid oracetylacetone, and the phenylpyridine may be substituted with an alkylgroup;

m represents 1 to 3; and

n represents 0 to 2, provided that m+n is 3:

in Formula (D-3), M represents iridium;

each of R₃ to R₆ independently represents a hydrogen atom, an alkylgroup or an aryl group;

each of R₃′ to R₈′ independently represents a hydrogen atom, an alkylgroup or an aryl group;

(X—Y) represents a ligand of phenylpyridine, picolinic acid oracetylacetone, and the phenylpyridine may be substituted with an alkylgroup;

m represents 1 to 3; and

n represents 0 to 2, provided that m+n is 3.

<8>

A light emitting layer, comprising:

at least each one of a compound represented by the following Formula(7), (8) or (11) and a compound represented by the following Formula(D-4), (D-2) or (D-3):

wherein R₇₁ to R₇₈ represent a hydrogen atom; and

each of Y₇₁ and Y₇₂ independently represents a group represented by thefollowing Formula (10):

wherein R₈₁ to R₈₈ represent a hydrogen atom; and

each of Y₈₁ and Y₈₂ independently represents a group represented by thefollowing Formula (10):

wherein R₁₁₃ represents a group represented by the following Formula(10);

R₁₁₁, R₁₁₂, R₁₁₄ and R₁₁₅ represent a hydrogen atom;

R₁₁₆ represents a hydrogen atom, an alkyl group or an aromatichydrocarbon ring group; and

m represents 2:

wherein R₁₀₁ to R₁₀₃ represent a hydrogen atom; and

R₁₀₄ represents a benzene ring, a biphenyl ring or a pyridine ring, andthese rings may be further substituted with an alkyl group having 1 to 6carbon atoms, a phenyl group or a pyridyl group:

in Formula (D-4), M represents iridium;

each of R₃ to R₁₀ independently represents a hydrogen atom, an alkylgroup or an aryl group;

each of R₃′ to R₆′ independently represents a hydrogen atom, an alkylgroup or an aryl group;

(X—Y) represents a ligand of phenylpyridine, picolinic acid oracetylacetone, and the phenylpyridine may be substituted with an alkylgroup;

m represents 1 to 3; and

n represents 0 to 2, provided that m+n is 3:

in Formula (D-2), M represents iridium;

each of R₃ to R₆ independently represents a hydrogen atom, an alkylgroup or an aryl group;

R₃′ to R₈′ represent a hydrogen atom, an alkyl group or an aryl group;(X—Y) represents a ligand of phenylpyridine, picolinic acid oracetylacetone, and the phenylpyridine may be substituted with an alkylgroup;

m represents 1 to 3; and

n represents 0 to 2, provided that m+n is 3:

in Formula (D-3), M represents iridium;

each of R₃ to R₆ independently represents a hydrogen atom, an alkylgroup or an aryl group;

each of R₃′ to R₈′ independently represents a hydrogen atom, an alkylgroup or an aryl group;

(X—) represents a ligand of phenylpyridine, picolinic acid oracetylacetone, and the phenylpyridine may be substituted with an alkylgroup;

m represents 1 to 3; and

n represents 0 to 2, provided that m+n is 3.

<9>

A light emission apparatus using the organic electroluminescence deviceas described in any one of <I> to <6>.

<10>

A display apparatus using the organic electroluminescence device asdescribed in any one of <1> to <6>.

<11>

An illumination apparatus using the organic electroluminescence deviceas described in any one of <1> to <6>.

Effects of the Invention

According to the present invention, it is possible to provide an organicelectroluminescence device having excellent light emission efficiencyand durability (in particular, durability when driving at a hightemperature).

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic view illustrating an example (first exemplaryembodiment) of a layer configuration of an organic EL device accordingto the present invention.

FIG. 2 is a schematic view illustrating an example (second exemplaryembodiment) of a light emission apparatus according to the presentinvention.

FIG. 3 is a schematic view illustrating an example (third exemplaryembodiment) of an illumination apparatus according to the presentinvention.

EMBODIMENTS FOR CARRYING OUT THE INVENTION

An organic electroluminescence device of the present invention includes,on a substrate, a pair of electrodes and at least one layer of anorganic layer including a light emitting layer containing a lightemitting material disposed between the electrodes, wherein the lightemitting layer contains at least each one of a compound represented bythe following Formula (3) and a compound represented by the followingFormula (D-1).Z³—(Y³)_(n) ₃   (3)

(wherein Z³ represents benzene, pyridine, triazine, pyrimidine,biphenyl, phenylpyridine, bipyridine, a silicon atom or a carbon atom,and may be further substituted with at least one group selected from analkyl group, an aryl group, a silyl group, a cyano group, a fluorineatom or a combination thereof. Y³ represents a group represented by thefollowing Formula (3a-1) or (3a-2). n³ represents an integer of 1 to 4.)

(In Formulas (3a-1) and (3a-2), the ring A represents an aromatic ringor a heterocyclic ring, represented by Formula (3b), which is condensedwith an adjacent ring, and the ring B represents a heterocyclic ringrepresented by Formula (3c), which is condensed with an adjacent ring.X³ represents C—R″ (R″ represents a hydrogen atom or a substituent) or anitrogen atom. Each of R₃₄ and R₃₁₁ independently represents a benzenering, a naphthalene ring, a pyridine ring, a triazine ring or apyrimidine ring, and these rings may be further substituted with atleast one group selected from a methyl group, an isobutyl group, at-butyl group, a neopentyl group, a phenyl group, a naphthyl group, acyano group and a fluorine atom. R₃₃ represents a hydrogen atom. Each ofR₃₁ and R₃₂ independently represents a hydrogen atom, an alkyl group, asilyl group, a fluorine atom, a cyano group or a trifluoromethyl group,and these groups may be further substituted with at least one of analkyl group having 1 to 6 carbon atoms and a phenyl group, ifpossible. * represents a bond for linking to Z³.)

(In Formula (D-1), M represents iridium. Each of R₃ to R₆ independentlyrepresents a hydrogen atom, an alkyl group or an aryl group. R₃′represents a hydrogen atom, an alkyl group or an aryl group. The ring Qrepresents a pyridine ring, a quinoline ring or an isoquinoline ring,which is coordinated to iridium, and may be further substituted with analkyl group or an aryl group. R₅ represents an aryl group or aheteroaryl group when the ring Q is a pyridine ring, and the aryl groupor the heteroaryl group may be further substituted with an alkyl group.R₃′ and R₆ may be linked to each other by a linking group selected from—CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —O—CR₂—, —NR—CR₂— and —N═CR— toform a ring, each R independently represents a hydrogen atom, an alkylgroup, an alkenyl group, an alkynyl group, an aryl group or a heteroarylgroup, and may further have a substituent selected from a halogen atom,—R′, —OR′, —N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)₂, —CN, —NO₂,—SO₂, —SOR′, —SO₂R′ and —SO₃R′, and each R′ independently represents ahydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group,an alkynyl group, an aryl group or a heteroaryl group. (X—Y) representsa ligand represented by any one of the following Formulas (1-1), (I-4)or (1-15). m represents an integer of 1 to 3, and n represents aninteger of 0 to 2. However, m+n is 3.)

(In Formulas (1-1), (1-4) and (1-15), each of Rx, Ry and Rzindependently represents a hydrogen atom, an alkyl group, aperfluoroalkyl group, a halogen atom or an aryl group.)

The organic electroluminescence device of the present invention containsat least each one of the compound represented by Formula (3) and thecompound represented by Formula (D-1), and accordingly, is able to havehigh light emission efficiency (for example, external quantumefficiency) and provide an organic electroluminescence device havinghigh durability.

First, an organic electroluminescence device including, on a substrate,a pair of electrodes and at least one layer of an organic layerincluding a light emitting layer containing a light emitting materialdisposed between the electrodes, wherein the light emitting layercontains at least each one of a compound represented by the followingFormula (1) and a compound represented by the following Formula (D-1)will be described.

(wherein the ring A represents an aromatic ring or a heterocyclic ringrepresented by Formula (1a), which is condensed with an adjacent ring,the ring B represents a heterocyclic ring represented by Formula (1b),which is condensed with an adjacent ring, X¹ represents carbon ornitrogen, each of R₁₁ and R₁₅ independently represents a substituted orunsubstituted aromatic hydrocarbon group or aromatic heterocyclic group,which is not a condensed ring structure other than a naphthalene ring,R₁₄ represents hydrogen, a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group, which is not acondensed ring structure, or a ring which is condensed with a ringincluding X¹, and each of R₁₂ and R₁₃ independently represents ahydrogen atom or a substituent.)

(In Formula (D-1), M represents a metal having an atomic weight of 40 ormore. Each of R₃ to R₆ independently represents a hydrogen atom or asubstituent. R₃′ represents a hydrogen atom or a substituent. The ring Qrepresents a pyridine ring, a quinoline ring or an isoquinoline ring,which is coordinated to the metal M, and may be further substituted witha non-aromatic group. R₅ represents an aryl group or a heteroaryl groupwhen the ring Q is a pyridine ring. R₃′ and R₆ may be linked to eachother by a linking group selected from —CR₂—CR₂—, —CR═CR—, —CR₂—, —O—,—NR—, —O—CR₂—, —NR—CR₂— and —N═CR— to form a ring, each R independentlyrepresents a hydrogen atom, an alkyl group, an alkenyl group, an alkynylgroup, a heteroalkyl group, an aryl group or a heteroaryl group, and mayfurther have a substituent selected from a halogen atom, —R′, —OR′,—N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)_(N)(R′)₂, —CN, —NO₂, —SO₂,—SOR′, —SO₂R′ and —SO₃R′, and each R′ independently represents ahydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group,an alkynyl group, a heteroalkyl group, an aryl group or a heteroarylgroup. (X—Y) represents an ancillary ligand. m represents a value of 1to the greatest number of ligands that may be bound to the metal, and nrepresents a value of 0 to the greatest number of ligands that may bebound to the metal. The value represents a value of the greatest numberof ligands that may be bound to the metal or less. m+n is the greatestnumber of ligands that may be bound to the metal.)

[A compound represented by Formula (1)]

A compound represented by Formula (1) will be described in detail.

(wherein the ring A represents an aromatic ring or a heterocyclic ringrepresented by Formula (1a), which is condensed with an adjacent ring,the ring B represents a heterocyclic ring represented by Formula (1b),which is condensed with an adjacent ring, X¹ represents carbon ornitrogen, each of R₁₁ and R₁₅ independently represents a substituted orunsubstituted aromatic hydrocarbon group or aromatic heterocyclic group,which is not a condensed ring structure other than a naphthalene ring,R₁₄ represents hydrogen, a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group, which is not acondensed ring structure, or a ring which is condensed with a ringincluding X¹, and each of R₁₂ and R₁₃ independently represents ahydrogen atom or a substituent.)

The compound represented by Formula (1) is a heterocyclic compoundcontaining an indolocarbazole structure in which an indole structure iscondensed with a carbazole structure. The compound represented byFormula (1), which is highly condensed in this manner, has more extendedconjugation than carbazole compounds in the related art, and thus, theelectron injection property may be improved while the hole injectionproperty is maintained, and the balance of electric charges in theorganic electroluminescence device may be improved. In particular, whenthe light emitting layer has excessive holes, these compounds are usedto facilitate electron injection into the light emitting layer andimprove the electric charge balance in the light emitting layer, therebyrealizing high efficiency and low voltage driving of the organicelectroluminescence device.

Further, the compound represented by Formula (1) has an extendedp-conjugated plane and has a small degree of freedom of molecularmotion, compared to carbazole compounds of the related art, and thus, itis assumed that the service life of the device is easily shortened byassociation and aggregation. When the compound represented by Formula(1) is used as a host material, it was thought that it was preferable touse a light emitting material which had a large degree of freedom, andthus, it was difficult to be condensed and associated in order torealize high durability of the device.

If materials having a small degree of freedom of molecular motion arecombined, it is thought that interaction between molecules (host-lightemitting material or between hosts, between light emitting materials, inany case), such as p-stacking, and the like, may not be overcome, andthus, it becomes easy to form an aggregation-association body.

When the compound represented by Formula (D-1) has many aromatic ringsand a condensed ring structure such as a quinoline ring and anisoquinoline ring, the degree of freedom of molecular motion isparticularly decreased, and thus, when the compound represented byFormula (1) is used as a host, it was expected that the compound wasinappropriate as a light emitting material. However, in the presentinvention, unexpectedly, the aggregation and association was notgenerated, and thus, the device durability was improved when driving ata high temperature by using the compound represented by Formula (D-1),which has a small degree of freedom of molecular motion, in combinationwith the compound represented by Formula (1), which has a small degreeof freedom of molecular motion.

Although it is not clear why the aggregation and association is notgenerated, it is understood that the permittivity and surface energy ofhost and guest materials are similar, and thus, the materials are notseparated in a film, and a homogeneous amorphous film is produced.

Further, it is considered that the device durability is improved whendriving at a high temperature because a mutual degradation reactionbetween host-host materials or between host-guest materials issuppressed by using hosts and guests which have a small degree offreedom of molecular motion.

X¹ in Formula (1) represents C—R″ (R″ represents a hydrogen atom or asubstituent) or a nitrogen atom. When R″ represents a substituent, thesubstituent may be exemplified by the following group A of substituents.Since chemical stability of Formula (1) is improved and the service lifeof the device is increased, X¹ is preferably C—H.

As substituents represented by R₁₂ and R₁₃ in Formula (1), thoseexemplified by the following group A of substituents may be applied.

(Group A of Substituents)

An alkyl group (having preferably 1 to 30 carbon atoms, more preferably1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms,and examples thereof include methyl, ethyl, isopropyl, tert-butyl,n-octyl, n-decyl, n-hexadecyl and the like), an alicyclic hydrocarbongroup (having preferably 1 to 30 carbon atoms, more preferably 1 to 20carbon atoms, and particularly preferably 1 to 10 carbon atoms, andexamples thereof include adamantyl, cyclopropyl, cyclopentyl, cyclohexyland the like), an alkenyl group (having preferably 2 to 30 carbon atoms,more preferably 2 to 20 carbon atoms, and particularly preferably 2 to10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl,3-pentenyl and the like), an alkynyl group (having preferably 2 to 30carbon atoms, more preferably 2 to 20 carbon atoms, and particularlypreferably 2 to 10 carbon atoms, and examples thereof include propargyl,3-pentynyl and the like), an aryl group (having preferably 6 to 30carbon atoms, more preferably 6 to 20 carbon atoms, and particularlypreferably 6 to 12 carbon atoms, and examples thereof include phenyl,p-methylphenyl, naphthyl, anthranyl and the like), an amino group(having preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbonatoms, and particularly preferably 0 to 10 carbon atoms, and examplesthereof include amino, methylamino, dimethylamino, diethylamino,dibenzylamino, diphenylamino, ditolylamino and the like), an alkoxygroup (having preferably 1 to 30 carbon atoms, more preferably 1 to 20carbon atoms, and particularly preferably 1 to 10 carbon atoms, andexamples thereof include methoxy, ethoxy, butoxy, 2-ethylhexyloxy andthe like), an aryloxy group (having preferably 6 to 30 carbon atoms,more preferably 6 to 20 carbon atoms, and particularly preferably 6 to12 carbon atoms, and examples thereof include phenyloxy, 1-naphthyloxy,2-naphthyloxy and the like), a heterocyclic oxy group (having preferably1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, andparticularly preferably 1 to 12 carbon atoms, and examples thereofinclude pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy and the like),an acyl group (having preferably 1 to 30 carbon atoms, more preferably 1to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms,and examples thereof include acetyl, benzoyl, formyl, pivaloyl and thelike), an alkoxycarbonyl group (having preferably 2 to 30 carbon atoms,more preferably 2 to 20 carbon atoms, and particularly preferably 2 to12 carbon atoms, and examples thereof include methoxycarbonyl,ethoxycarbonyl and the like), an aryloxycarbonyl group (havingpreferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms,and particularly preferably having 7 to 12 carbon atoms, and examplesthereof include phenyloxycarbonyl and the like), an acyloxy group(having preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbonatoms, and particularly preferably 2 to 10 carbon atoms, and examplesthereof include acetoxy, benzoyloxy and the like), an acylamino group(having preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbonatoms, and particularly preferably 2 to 10 carbon atoms, and examplesthereof include acetylamino, benzoylamino and the like), analkoxycarbonylamino group (having preferably 2 to 30 carbon atoms, morepreferably 2 to 20 carbon atoms, and particularly preferably 2 to 12carbon atoms, and examples thereof include methoxycarbonylamino and thelike), an aryloxycarbonylamino group (having preferably 7 to 30 carbonatoms, more preferably 7 to 20 carbon atoms, and particularly preferably7 to 12 carbon atoms, and examples thereof includephenyloxycarbonylamino and the like), a sulfonylamino group (havingpreferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms,and particularly preferably 1 to 12 carbon atoms, and examples thereofinclude methanesulfonylamino, benzenesulfonylamino and the like), asulfamoyl group (having preferably 0 to 30 carbon atoms, more preferably0 to 20 carbon atoms, and particularly preferably 0 to 12 carbon atoms,and examples thereof include sulfamoyl, methylsulfamoyl,dimethylsulfamoyl, phenylsulfamoyl and the like), a carbamoyl group(having preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbonatoms, and particularly preferably 1 to 12 carbon atoms, and examplesthereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl,phenylcarbamoyl and the like), an alkylthio group (having preferably 1to 30 carbon atoms, more preferably 1 to 20 carbon atoms, andparticularly preferably 1 to 12 carbon atoms, and examples thereofinclude methylthio, ethylthio and the like), an arylthio group (havingpreferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms,and particularly preferably 6 to 12 carbon atoms, and examples thereofinclude phenylthio and the like), a heterocyclic thio group (havingpreferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms,and particularly preferably 1 to 12 carbon atoms, and examples thereofinclude pyridylthio, 2-benzimizolylthio, 2-benzoxazolylthio,2-benzthiazolylthio and the like), a sulfonyl group (having preferably 1to 30 carbon atoms, more preferably 1 to 20 carbon atoms, andparticularly preferably 1 to 12 carbon atoms, and examples thereofinclude mesyl, tosyl and the like), a sulfinyl group (having preferably1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, andparticularly preferably 1 to 12 carbon atoms, and examples thereofinclude methanesulfinyl, benzenesulfinyl and the like), a ureido group(having preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbonatoms, and particularly preferably 1 to 12 carbon atoms, and examplesthereof include ureido, methylureido, phenylureido and the like), aphosphoric acid amide group (having preferably 1 to 30 carbon atoms,more preferably 1 to 20 carbon atoms, and particularly preferably 1 to12 carbon atoms, and examples thereof include diethylphosphoric acidamide, phenylphosphoric acid amide and the like), a hydroxyl group, amercapto group, a halogen atom (for example, a fluorine atom, a chlorineatom, a bromine atom and an iodine atom), a cyano group, a sulfo group,a carboxyl group, a nitro group, a hydroxamic acid group, a sulfinogroup, a hydrazino group, an imino group, a heterocyclic group (havingpreferably 1 to 30 carbon atoms, and more preferably 1 to 12 carbonatoms, and examples of the heteroatom include a nitrogen atom, an oxygenatom, and a sulfur atom, and specifically imidazolyl, pyridyl, quinolyl,furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl,benzthiazolyl, a carbazolyl group, an azepinyl group and the like), asilyl group (having preferably 3 to 40 carbon atoms, more preferably 3to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms,and examples thereof include trimethylsilyl, triphenylsilyl, and thelike), a silyloxy group (having preferably 3 to 40 carbon atoms, morepreferably 3 to 30 carbon atoms, and particularly preferably 3 to 24carbon atoms, and examples thereof include trimethylsilyloxy,triphenylsilyloxy and the like)

R₁₂ and R₁₃ include preferably a hydrogen atom, an alkyl group, analicyclic hydrocarbon group, an aryl group, a fluorine group, an aminogroup, an alkoxy group, an aryloxy group, a heterocyclic oxy group, analkylthio group, an arylthio group, a heterocyclic thio group, a cyanogroup, a heterocyclic group, a silyl group, a silyloxy group and atrifluoromethyl group, more preferably a hydrogen atom, an alkyl group,an alicyclic hydrocarbon group, an aryl group, a fluorine group, a cyanogroup, a silyl group, a heterocyclic group and a trifluoromethyl group,even more preferably a hydrogen atom, an alkyl group, an aryl group, afluorine group, a cyano group, a silyl group and a trifluoromethylgroup, and particularly preferably a hydrogen atom, an alkyl group, asilyl group, a fluorine group, a cyano group and a trifluoromethylgroup.

R₁₂ and R₁₃ may further have a substituent, and the above-describedgroup A of substituents may be applied as the substituent, whichincludes an alkyl group, an aryl group, a cyano group, a halogen atomand a nitrogen-containing aromatic heterocyclic group, more preferablyalkyl having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbonatoms, a pyridyl group and a fluorine atom, and more preferably an alkylgroup having 1 to 6 carbon atoms and a phenyl group. The number ofsubstituents may be 0 to 4, and preferably 0 to 2. Further, a pluralityof substituents may be linked to each other to form a ring.

In Formula (1), a substituted or unsubstituted aromatic hydrocarbongroup or aromatic heterocyclic group, which is not a condensed ringstructure other than a naphthalene ring, represented by R₁₁ and R₁₅,includes a benzene ring, a naphthalene ring, a biphenyl ring, ano-terphenyl ring, an m-terphenyl ring, a p-terphenyl ring, a furan ring,a thiophene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring,a pyrazine ring, a triazine ring, an oxadiazole ring, a triazole ring,an imidazole ring, a pyrazole ring, a thiazole ring and the like.

R₁₁ and R₁₅ include preferably a benzene ring, a naphthalene ring, abiphenyl ring, a pyrazole ring, an imidazole ring, a triazole ring, apyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, atriazine ring and a thiophene ring, more preferably a benzene ring, anaphthalene ring, a biphenyl ring, a pyridine ring, a pyrimidine ringand a triazine ring, even more preferably a benzene ring, a naphthalenering, a pyridine ring, a triazine ring and a pyrimidine ring,particularly preferably a benzene ring, a pyridine ring and a triazinering, and most preferably a benzene ring and a pyridine ring.

R₁₁ and R₁₅ may further have a substituent, and the above-describedgroup A of substituents may be applied as the substituent, and includespreferably an alkyl group, an aryl group, a cyano group, a halogen atom,and a nitrogen-containing aromatic heterocyclic group, more preferablyalkyl having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbonatoms, pyridyl, a cyano group and a halogen atom, even more preferably abranched alkyl group having 3 to 6 carbon atoms, a phenyl group, anaphthyl group, a cyano group and a fluorine atom, and particularlypreferably a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group and afluorine atom. The number of substituents may be 0 to 4, and preferably0 to 2. Further, a plurality of substituents may be linked to each otherto form a ring.

A substituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group, which is not a condensed ring structure, representedby R₁₄, includes a benzene ring, a biphenyl ring, an o-terphenyl ring,an m-terphenyl ring, a p-terphenyl group, a furan ring, a thiophenering, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazinering, an oxadiazole ring, a triazole ring, an imidazole ring, a pyrazolering, a thiazole ring and the like. The aromatic heterocycling ring mayhave a substituent, and as the substituent, those exemplified above forthe group A of substituents may be applied.

R₁₄ includes preferably a hydrogen atom, a benzene ring, a biphenylring, a pyrazole ring, an imidazole ring, a triazole ring, a pyridinering and a thiophene ring, more preferably a hydrogen atom, a benzenering, a biphenyl ring and a pyridine ring, and particularly preferably ahydrogen atom.

R₁₄ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied, andmay include preferably an alkyl group having 1 to 6 carbon atoms, aphenyl group, a pyridyl group and the like.

Further, a plurality of substituents may be linked to a ring includingX′ to form a ring.

The compound represented by Formula (3) is preferably represented byFormula (1). In this case, in Formula (1), the ring A represents anaromatic ring or a heterocyclic ring represented by Formula (1a), whichis condensed with an adjacent ring, and the ring B represents aheterocyclic ring represented by Formula (1b), which is condensed withan adjacent ring. X¹ represents C—R″ (R″ represents a hydrogen atom or asubstituent) or a nitrogen atom. Each of R₁₁ and R₁₅ independentlyrepresents a benzene ring, a naphthalene ring, a pyridine ring, atriazine ring or a pyrimidine ring, and these rings may be furthersubstituted with at least one group selected from a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom. R₁₄ represents ahydrogen atom. Each of R₁₂ and R₁₃ independently represents a hydrogenatom, an alkyl group, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, and these groups may be further substituted withat least one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup.

A preferred range of each symbol in the above definition is the same asthat described above.

As the compound represented by Formula (1), one of preferable forms is acompound represented by the following Formula (2).

(wherein the ring C represents an aromatic ring or a heterocyclic ringrepresented by Formula (2a), which is condensed with an adjacent ring,the ring D represents a heterocyclic ring represented by Formula (2b),which is condensed with an adjacent ring, the ring E represents aheterocyclic ring represented by Formula (2c), which is condensed withan adjacent ring, X² represents carbon or nitrogen, each of R₂₁, R₂₆ andR₂₇ independently represents a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group, which is not acondensed ring structure other than a naphthalene ring, R₂₅ representshydrogen, a substituted or unsubstituted aromatic hydrocarbon group oraromatic heterocyclic group, which is not a condensed ring structure, ora ring which is condensed with a ring including X², and each of R₂₂, R₂₃and R₂₄ independently represents a hydrogen atom or a substituent.)

Each of R₂₁, R₂₆ and R₂₇ independently represents a substituted orunsubstituted aromatic hydrocarbon group or aromatic heterocyclic group,which is not a condensed ring structure other than a naphthalene ring,and has the same meaning as R₁₁ and R₁₅ in Formula (1), and preferredranges thereof are also the same.

R₂₅ represents hydrogen, a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group, which is not acondensed ring structure, or a ring which is condensed with a ringincluding X², and has the same meaning as R₁₄ in Formula (1), andpreferred ranges thereof are also the same.

Each of R₂₂, R₂₃ and R₂₄ independently represents a hydrogen atom or asubstituent, and has the same meaning as R₁₂ and R₁₃ in Formula (1), andpreferred ranges thereof are also the same.

As the compound represented by Formula (1), one of the preferable formsis a compound represented by the following Formula (15).

(wherein X₁₅₁ to X₁₅₃ represent a nitrogen atom or C—R₁₅₃, and R₁₅₃represents a hydrogen atom, a methyl group, an isobutyl group, a t-butylgroup, a neopentyl group, a phenyl group, a naphthyl group, a cyanogroup or a fluorine atom. Each of R₁₅₁ and R₁₅₂ independently representsa hydrogen atom, a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group or afluorine atom. Y¹⁵ represents a group represented by any one of thefollowing Formulas (15a) to (15c).)

(wherein R₁₅₅ represents a hydrogen atom. Each of R₁₅₄ and R₁₅₆independently represents a hydrogen atom, an alkyl group, a silyl group,a fluorine atom, a cyano group or a trifluoromethyl group, and thesegroups may be further substituted with at least one of an alkyl grouphaving 1 to 6 carbon atoms and a phenyl group. R₁₅₇ represents a benzenering, a naphthalene ring, a pyridine ring, a triazine ring or apyrimidine ring, and these rings may be further substituted with atleast one group selected from a methyl group, an isobutyl group, at-butyl group, a neopentyl group, a phenyl group, a naphthyl group, acyano group and a fluorine atom.)

X₁₅₁ to X₁₅₃ represent a nitrogen atom or C—R₁₅₃, and R₁₅₃ represents ahydrogen atom or a substituent. A combination of X₁₅₁ to X₁₅₃ is notparticularly limited, but the number of nitrogen atoms is preferably 0,1 or 3, and more preferably 0 or 3.

As the substituent represented by R₁₅₁ and R₁₅₂, those exemplified abovefor the group A of substituents may be applied.

R₁₅₁ and R₁₅₂ include preferably a hydrogen atom, an alkyl group, analicyclic hydrocarbon group, an aryl group, a fluorine group, an aminogroup, an alkoxy group, an aryloxy group, a heterocyclic oxy group, analkylthio group, an arylthio group, a heterocyclic thio group, a cyanogroup, a heterocyclic group, a silyl group and a silyloxy group, morepreferably a hydrogen atom, an alkyl group, an alicyclic hydrocarbongroup, an aryl group, a fluorine group, a cyano group, a silyl group anda heterocyclic group, even more preferably a hydrogen atom, an alkylgroup (preferably a methyl group, an isobutyl group, a t-butyl group anda neopentyl group), an aryl group (preferably a phenyl group and anaphthyl group), a cyano group and a fluorine atom, and particularlypreferably a hydrogen atom, an alkyl group and aryl group.

R₁₅₁ and R₁₅₂ may further have a substituent, and as the substituent,those exemplified above for the group A of substituents may be applied,and may include preferably alkyl having 1 to 6 carbon atoms, phenyl,pyridyl and the like. The number of substituents is preferably 0 to 4,and more preferably 0 to 2. Further, a plurality of substituents may belinked to each other to form a ring.

As the substituent represented by R₁₅₃, those exemplified above for thegroup A of substituents may be applied.

R₁₅₃ includes preferably a hydrogen atom, an alkyl group, an alicyclichydrocarbon group, an aryl group, a fluorine group, an amino group, analkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthiogroup, an arylthio group, a heterocyclic thio group, a cyano group, aheterocyclic group, a silyl group and a silyloxy group, more preferablya hydrogen atom, an alkyl group, an alicyclic hydrocarbon group, an arylgroup, a fluorine group, a cyano group, a silyl group and a heterocyclicgroup, even more preferably a hydrogen atom, an alkyl group (preferablya methyl group, an isobutyl group, a t-butyl group and a neopentylgroup), an aryl group (preferably a phenyl group and a naphthyl group),a cyano group, a fluorine atom, a hydrogen atom, an alkyl group and anaryl group, particularly preferably a hydrogen atom and an alkyl group,and most preferably a hydrogen atom.

R₁₅₃ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied, andmay include preferably alkyl having 1 to 6 carbon atoms, phenyl, pyridyland the like. The number of substituents is preferably 0 to 4, and morepreferably 0 to 2. Further, a plurality of substituents may be linked toeach other to form a ring.

Y¹⁵ represents a group represented by any one of Formulas (15a) to(15c), preferably (15a) and (15b), and more preferably (15a).

In Formulas (15a) to (15c), as the substituent represented by R₁₅₄ andR₁₅₆, those exemplified above for the group A of substituents may beapplied.

R₁₅₄ and R₁₅₆ include preferably a hydrogen atom, an alkyl group, analicyclic hydrocarbon group, an aryl group, a fluorine group, an aminogroup, an alkoxy group, an aryloxy group, a heterocyclic oxy group, analkylthio group, an arylthio group, a heterocyclic thio group, a cyanogroup, a heterocyclic group, a silyl group and a silyloxy group, morepreferably a hydrogen atom, an alkyl group, an alicyclic hydrocarbongroup, an aryl group, a fluorine group, a cyano group, a silyl group anda heterocyclic group, even more preferably a hydrogen atom, an alkylgroup and an aryl group, particularly preferably a hydrogen atom and analkyl group, and most preferably a hydrogen atom.

R₁₅₄ and R₁₅₆ may further have a substituent, and as the substituent,those exemplified above for the group A of substituents may be applied,and may include preferably alkyl having 1 to 6 carbon atoms, phenyl,pyridyl and the like. The number of substituents is preferably 0 to 4,and more preferably 0 to 2. Further, a plurality of substituents may belinked to each other to form a ring.

A substituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group, which is not a condensed ring structure, representedby R₁₅₅, includes a benzene ring, a biphenyl ring, an o-terphenyl ring,an m-terphenyl ring, a p-terphenyl ring, a furan ring, a thiophene ring,a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring,an oxadiazole ring, a triazole ring, an imidazole ring, a pyrazole ring,a thiazole ring and, the like. The aromatic heterocyclic ring may have asubstituent, and as the substituent, those exemplified above for thegroup A of substituents may be applied.

R₁₅₅ includes preferably a hydrogen atom, a benzene ring, a biphenylring, a pyrazole ring, an imidazole ring, a triazole ring, a pyridinering and a thiophene ring, more preferably a hydrogen atom, a benzenering, a biphenyl ring and a pyridine ring, and particularly preferably ahydrogen atom.

R₁₅₅ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied, andmay include preferably alkyl having 1 to 6 carbon atoms, phenyl, pyridyland the like.

A substituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group, which is not a condensed ring structure other than anaphthalene ring, represented by R₁₅₇, includes a benzene ring, anaphthalene ring, a biphenyl ring, an o-terphenyl ring, an m-terphenylring, a p-terphenyl ring, a furan ring, a thiophene ring, a pyridinering, a pyridazine ring, a pyrimidine ring, a pyrazine ring, anoxadiazole ring, a triazole ring, an imidazole ring, a pyrazole ring, athiazole ring and the like. The aromatic heterocyclic ring may have asubstituent, and as the substituent, those exemplified above for thegroup A of substituents may be applied.

R₁₅₇ includes preferably a benzene ring, a biphenyl ring, a pyrazolering, an imidazole ring, a triazole ring, a pyridine ring, a thiophenering, a naphthalene ring, and a triazine ring, more preferably a benzenering, a biphenyl ring, a pyridine ring, a naphthalene ring and atriazine ring, particularly preferably a benzene ring, a naphthalenering, a pyridine ring, a naphthalene ring, and a triazine ring,particularly preferably a benzene ring and a triazine ring, and mostpreferably a benzene ring.

R₁₅₇ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied, andmay include preferably alkyl having 1 to 6 carbon atoms, phenyl, pyridyland the like. The number of substituents is preferably 0 to 4, and morepreferably 0 to 2. Further, a plurality of substituents may be linked toeach other to form a ring.

As the compound represented by Formula (15), one of the preferable formsis a compound represented by the following Formula (16).

(wherein X₁₆₁ to X₁₆₃ represents a nitrogen atom or C—H, and each ofR₁₆₁ and R₁₆₂ independently represents a hydrogen atom or a substituent.Y¹⁶ represents a group represented by any one of the following Formulas(15a) to (15c).)

R₁₆₁, R₁₆₂ and Y¹⁶ have the same meaning as R₁₅₁, R₁₅₂ and Y¹⁵ inFormula (15), and preferred ranges thereof are also the same.

X₁₆₁ to X₁₆₃ represent a nitrogen atom or C—H. A combination of X₁₅₁ toX₁₅₃ is not particularly limited, but the number of nitrogen atoms ispreferably 0, 1 or 3 and more preferably 0 or 3.

In the above Formula, it is preferred that X₁₆₁ to X₁₆₃ represents anitrogen atom or C—H, each of R₁₆₁ and R₁₆₂ independently represents ahydrogen atom, a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group or afluorine atom, and Y¹⁶ represents a group represented by any one ofFormulas (15a) to (15c).

As the compound represented by Formula (16), one of the preferable formsis a compound represented by the following Formula (17).

(wherein each of R₁₇₁ to R₁₇₂ independently represents a hydrogen atomor a substituent. Y¹⁷ represents a group represented by any one ofFormulas (15a) to (15c).)

R₁₇₁, R₁₇₂ and Y¹⁷ have the same meaning as R₁₆₁, R₁₆₂ and Y¹⁶ inFormula (16), and preferred ranges thereof are also the same.

In the above Formula, it is preferred that each of R₁₇₁ and R₁₇₂independently represents a hydrogen atom, a methyl group, an isobutylgroup, a t-butyl group, a neopentyl group, a phenyl group, a naphthylgroup, a cyano group or a fluorine atom, and Y¹⁷ represents a grouprepresented by any one of Formulas (15a) to (15c).

As the compound represented by Formula (16), one of the preferable formsis a compound represented by the following Formula (18).

(wherein each of R₁₈₁ and R₁₈₂ independently represents a hydrogen atomor a substituent. Y¹⁸ represents a group represented by any one ofFormulas (15a) to (15c).)

R₁₈₁, R₁₈₂ and Y¹⁸ have the same meaning as R₁₆₁, R₁₆₂ and Y¹⁶ inFormula (16), an preferred ranges thereof are also the same.

In the above Formula, it is preferred that each of R₁₈₁ and R₁₈₂independently represents a hydrogen atom, a methyl group, an isobutylgroup, a t-butyl group, a neopentyl group, a phenyl group, a naphthylgroup, a cyano group or a fluorine atom, and Y′⁸ represents a grouprepresented by any one of Formulas (15a) to (15c).

As the compound represented by Formula (1) or (2), one of the preferableforms is a compound represented by the following Formula (3).Z³

Y³)_(n) ₃   (3)

(wherein Z³ represents a n³ valent group including a substituted orunsubstituted aromatic hydrocarbon group or aromatic heterocyclic groupwhich is not a condensed ring structure, a silicon atom or a carbonatom, Y³ represents a group represented by the following Formula (3a-1),(3a-2) or (3e), and n³ represents an integer of 1 or more.)

The substituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group represented by Z³, which is not a condensed ringstructure includes preferably benzene, pyridine, triazine, pyrimidine,biphenyl, phenylpyridine, bipyridine, terphenyl, triazole, diazole,phenyltriazole, triphenylthiazole and the like, preferably benzene,pyridine, triazine, pyrimidine, biphenyl, phenylpyridine and bipyridine,and more preferably a benzene ring, a biphenyl ring and a pyridine ring.When these have a substituent, the substituent may include a substituentselected from the group A of substituents, preferably at least one groupselected from an alkyl group, an aryl group, a silyl group, a cyanogroup, a fluorine atom, and a combination thereof, and more preferablyalkyl having 1 to 6 carbon atoms, phenyl and pyridyl. The number ofsubstituents may be 0 to 4, and preferably 0 to 2.

When Z³ represents a silicon atom or a carbon atom, the silicon atom andthe carbon atom may further have a substituent, if possible, and thesubstituent may include a substituent selected from the group A ofsubstituents, preferably at least one group selected from an alkylgroup, an aryl group, a silyl group, a cyano group, a fluorine atom anda combination thereof, more preferably at least one group selected froman alkyl group, an aryl group and a combination thereof, and even morepreferably a methyl group and a phenyl group.

Y³ represents a group represented by the following Formula (3a-1),(3a-2) or (3e).

(wherein the ring A represents an aromatic ring or a heterocyclic ringrepresented by Formula (3b), which is condensed with an adjacent ring,the ring B represents a heterocyclic ring represented by Formula (3c),which is condensed with an adjacent ring, X³ represents carbon ornitrogen, each of R₃₄ and R₃₁₁ independently represents a substituted orunsubstituted aromatic hydrocarbon group or aromatic heterocyclic group,which is not a condensed ring structure other than a naphthalene ring,R₃₃ represents hydrogen, a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group, which is not acondensed ring structure, or a ring which is condensed with a ringincluding X³, and each of R₃₁ and R₃₂ independently represents ahydrogen atom or a substituent. * represents a bond for linking to Z³.)

R₃₄ and R₃₁₁ represent a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group, which is not acondensed ring structure other than a naphthalene ring, and has the samemeaning as R₁₅ in Formula (1), and preferred ranges thereof are also thesame.

R₃₃ represents hydrogen, a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group, which is not acondensed ring structure, or a ring which is condensed with a ringincluding X, and has the same meaning as R₁₄ in Formula (1), andpreferred ranges thereof are also the same.

Each of R₃₁ and R₃₂ independently represents a hydrogen atom or asubstituent, and has the same meaning as R₁₂ and R₁₃ in Formula (1), andpreferred ranges thereof are also the same.

(wherein the ring C represents an aromatic ring or a heterocyclic ringrepresented by Formula (30, which is condensed with an adjacent ring,the ring D represents a heterocyclic ring represented by Formula (3g),which is condensed with an adjacent ring, the ring E represents aheterocyclic ring represented by Formula (3h), which is condensed withan adjacent ring, X³ represents carbon or nitrogen, each of R₃₉ and R₃₁₀independently represents a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group, which is not acondensed ring structure other than a naphthalene ring, R₃₈ representshydrogen, a substituted or unsubstituted aromatic hydrocarbon group oraromatic heterocyclic group, which is not a condensed ring structure, ora ring which is condensed with a ring including X³, and each of R₃₅, R₃₆and R₃₇ independently represents a hydrogen atom or a substituent.)

Each of R₃₉ and R₃₁₀ independently represents a substituted orunsubstituted aromatic hydrocarbon group or aromatic heterocyclic group,which is not a condensed ring structure other than a naphthalene ring,and has the same meaning as R₂₆ and R₂₇ in Formula (2), and preferredranges thereof are also the same.

R₃₈ represents hydrogen, a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group, which is not acondensed ring structure, or a ring which is condensed with a ringincluding X³, and has the same meaning as R₂₅ in Formula (2), andpreferred ranges thereof are also the same.

Each of R₃₅, R₃₆, and R₃₇ independently represents a hydrogen atom or asubstituent, and has the same meaning as Rn, R₂₃ and R₂₄ in Formula (1),and preferred ranges thereof are also the same.

n³ in Formula (3) is preferably 1 to 4, more preferably 2 to 4, and evenmore preferably 2 to 3.

One of the preferable forms of the compound represented by Formula (3)is a compound represented by the following Formula (4).Ar₄₁

Y⁴)₂  (4)

(wherein Ar₄₁ represents a divalent linking group consisting of asubstituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group, which is not a condensed ring structure, and Y⁴represents a group represented by Formula (3a-1), (3a-2) or (3e).)

Ar₄₁ in Formula (4) represents a divalent linking group. Specifically,the linking group may include a linking group represented by thefollowing Y-1 to Y-118.

Further, these linking groups may have a substituent. Examples of thesubstituent include an alkyl group, an aralkyl group, an alkenyl group,an alkynyl group, a cyano group, a dialkylamino group, a diarylaminogroup, a diaralkylamino group, an amino group, a nitro group, an acylgroup, an alkoxycarbonyl group, a carboxyl group, an alkoxyl group, analkylsulfonyl group, a halogen atom, a haloalkyl group, a hydroxylgroup, an amide group, and a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group.

Preferred examples of the substituent include a substituent representedby the following Z-1 to Z-138.

The substituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group represented by the linking group Ar₄₁, which is not acondensed ring structure includes preferably benzene, pyridine,triazine, pyrimidine, biphenyl, phenylpyridine, bipyridine, a terphenylring, a triazole ring, a diazole ring, a phenyltriazole ring, atriphenylthiazole ring and the like, more preferably benzene, pyridine,triazine, pyrimidine, biphenyl, phenylpyridine and bipyridine, and evenmore preferably a benzene ring, a biphenyl ring and a pyridine ring.When these have a substituent, the substituent may include a substituentselected from the group A of substituents, preferably at least one groupselected from an alkyl group, an aryl group, a silyl group, a cyanogroup, a fluorine atom and a combination thereof, and more preferablyalkyl having 1 to 6 carbon atoms, phenyl and pyridyl. The number ofsubstituents may be 0 to 4, and preferably 0 to 2.

Y⁴ represents a group represented by Formula (3a-1), (3a-2) or (3e).

One of the preferable forms of the compound represented by Formula (3)is a compound represented by the following Formula (5).

(wherein each of R₅₁ to R₅₆ independently represents a hydrogen atom ora substituent, but at least two of R₅₁ to R₅₆ are a group represented byFormula (3a-1), (3a-2) or (3e).)

Each of R₅₁ to R₅₆ independently represents a hydrogen atom or asubstituent and as the substituent, those exemplified above for theabove group A of substituents may be applied, but at least two of R₅₁ toR₅₆ are a group represented by Formula (3a-1), (3a-2) or (3e).

R₅₁ to R₅₆ include preferably a hydrogen atom, an alkyl group, analicyclic hydrocarbon group, an aryl group, a fluorine group, an aminogroup, an alkoxy group, an aryloxy group, a heterocyclic oxy group, analkylthio group, an arylthio group, a heterocyclic thio group, a cyanogroup, a heterocyclic group, a silyl group and a silyloxy group, morepreferably a hydrogen atom, an alkyl group, an alicyclic hydrocarbongroup, an aryl group, a fluorine group, a cyano group, a silyl group anda heterocyclic group, even more preferably a hydrogen atom, a methylgroup, an isobutyl group, a t-butyl group, a neopentyl group, a phenylgroup, a naphthyl group, a cyano group and a fluorine atom, particularlypreferably a hydrogen atom, a methyl group, a t-butyl group, a phenylgroup, a cyano group and a fluorine atom, preferably among them, ahydrogen atom, a methyl group, a phenyl group and a fluorine atom, andmost preferably a hydrogen atom.

R₅₁ to R₅₆ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied.Further, a plurality of substituents may be linked to each other to forma ring.

In Formula (5), it is preferred that at least two of Formulas R₅₁ to R₅₆are preferably (3a-1). At this time, (3a-1) which is one of Formula (5)is preferably substituted in the para position or meta position relativeto another (3a-1), and more preferably substituted in the meta position.

In the above Formula, each of R₅₁ to R₅₆ independently represents ahydrogen atom, a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group, afluorine atom or a group represented by any one of Formula (10), (10-2)or (10-3) as described below, but it is preferred that each of at leasttwo of R₅₁ to R₅₆ is independently a group represented by any one ofFormula (10), (10-2) or (10-3) as described below.

One of the preferable forms of the compound represented by Formula (3)is a compound represented by the following Formula (6).

(wherein each of R₆₁ to R₆₁₀ independently represents a hydrogen atom ora substituent. At least two of R₆₁ to R₆₁₀ is a group represented byFormula (3a-1), (3a-2) or (3e).

Each of R₆₁ to R₆₁₀ independently represents a hydrogen atom or asubstituent, and as the substituent, those exemplified above for thefollowing group A of substituents may be applied, but at least two ofR₆₁ to R₆₁₀ are a group represented by Formula (3a-1), (3a-2) or (3e).In Formula (6), it is preferred that at least one of Formulas R₆₁ to R₆₅is (3a-1), and at least one of Formulas R₆₆ to R₅₁₀ is (3a-1).

R₆₁ to R₆₁₀ include preferably a hydrogen atom, an alkyl group, analicyclic hydrocarbon group, an aryl group, a fluorine group, an aminogroup, an alkoxy group, an aryloxy group, a heterocyclic oxy group, analkylthio group, an arylthio group, a heterocyclic thio group, a cyanogroup, a heterocyclic group, a silyl group and a silyloxy group, morepreferably a hydrogen atom, an alkyl group, an alicyclic hydrocarbongroup, an aryl group, a fluorine group, a cyano group, a silyl group anda heterocyclic group, even more preferably a hydrogen atom, even morepreferably a hydrogen atom, a methyl group, an isobutyl group, a t-butylgroup, a neopentyl group, a phenyl group, a naphthyl group, a cyanogroup and a fluorine atom, particularly preferably a hydrogen atom, amethyl group, a t-butyl group, a phenyl group, a cyano group and afluorine atom, preferably among them, a hydrogen atom and a methylgroup, and most preferably a hydrogen atom.

R₆₁ to R₆₁₀ may further have a substituent, and as the substituent,those exemplified above for the group A of substituents may be applied.Further, a plurality of substituents may be linked to each other to forma ring.

In the above Formula, each of R₆₁ to R₆₁₀ independently represents ahydrogen atom, a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group, afluorine atom or a group represented by any one of Formula (10), (10-2)or (10-3) as described below, but it is preferred that each of at leasttwo of R₆₁ to R₆₁₀ is independently a group represented by any one ofFormula (10), (10-2) or (10-3) as described below.

One of the preferable forms of the compound represented by Formula (6)is a compound represented by the following Formula (7).

(wherein each of R₇₁ to R₇₈ independently represents a hydrogen atom ora substituent. Each of Y₇₁ and Y₇₂ independently represents a grouprepresented by Formula (3a-1), (3a-2) or (3e).)

Each of R₇₁ to R₇₈ independently represents a hydrogen atom or asubstituent, and is the same meaning as R₆₁ to R₆₁₀ in Formula (6), andpreferred ranges thereof are also the same.

In the above Formula, each of R₇₁ to R₇₈ independently represents ahydrogen atom, a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group, afluorine atom or a group represented by one of the following Formula(10), (10-2) or (10-3), and it is preferred that each of Y₇₁ and Y₇₂ isindependently a group represented by any one of the following Formula(10), (10-2) or (10-3).

One of the preferable forms of the compound represented by Formula (6)is a compound represented by the following Formula (8).

(wherein each of R₈₁ to R₈₈ independently represents a hydrogen atom ora substituent. Each of Y₈₁ and Y₈₂ independently represents a grouprepresented by Formula (3a-1), (3a-2) or (3e).)

Each of R₈₁ to R₈₈ independently represents a hydrogen atom or asubstituent, and has the same meaning as R₆₁ to R₆₁₀ in Formula (6), andpreferred ranges thereof are also the same.

In the above Formula, each of R₈₁ to R₈₈ independently represents ahydrogen atom, a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group, afluorine atom or a group represented by any one of Formula (10), (10-2)or (10-3) as described below, and it is preferred that each of Y₈₁ andY₈₂ is independently a group represented by any one of Formula (10),(10-2) or (10-3) as described below.

One of the preferable forms of the compound represented by Formula (3)is a compound represented by the following Formula (9).

(wherein each of R₉₁ to R₉₁₀ independently represents a hydrogen atom ora substituent, but at least two of R₉₁ to R₉₁₀ represents a grouprepresented by Formula (3a-1), (3a-2) or (3e). L₁ represents a divalentlinking group.)

Each of R₉₁ to R₉₁₀ independently represents a hydrogen atom or asubstituent, and as the substituent, those exemplified above for thefollowing group A of substituents may be applied, but at least two ofR₉₁ to R₉₁₀ are a group represented by Formula (3a-1), (3a-2) or (3e).In Formula (6), it is preferred that at least one of R₉₁ to R₉₅ isFormula (3a-1), and at least one of Formulas R₉₆ to R₉₁₀ is Formula(3a-1).

R₉₁ to R₉₁₀ include preferably a hydrogen atom, an alkyl group, analicyclic hydrocarbon group, an aryl group, a fluorine group, an aminogroup, an alkoxy group, an aryloxy group, a heterocyclic oxy group, analkylthio group, an arylthio group, a heterocyclic thio group, a cyanogroup, a heterocyclic group, a silyl group and a silyloxy group, morepreferably a hydrogen atom, an alkyl group, an alicyclic hydrocarbongroup, an aryl group, a fluorine group, a cyano group, a silyl group anda heterocyclic group, even more preferably a hydrogen atom, a methylgroup, an isobutyl group, a t-butyl group, a neopentyl group, a phenylgroup, a naphthyl group, a cyano group and a fluorine atom, particularlypreferably a hydrogen atom, a methyl group, a t-butyl group, a phenylgroup, a cyano group and a fluorine atom, preferably among them, ahydrogen atom, a methyl group and a fluorine atom, and most preferably ahydrogen atom.

R₉₁ to R₉₁₀ may further have a substituent, and as the substituent,those exemplified above for the group A of substituents may be applied.Further, a plurality of substituents may be linked to each other to forma ring.

The divalent linking group represented by L₁ may include a groupincluding a substituted silicon atom, a substituted germanium atom and aheteroatom (for example, a divalent group including a chalcogen atomsuch as —O—, —S— and the like, and an —N(R)— group wherein R representsa hydrogen atom or an alkyl group, wherein the alkyl group may be thesame as the alkyl group described as the group A of substituents) inaddition to a hydrocarbon group such as an alkylene group (for example,a methylene group, an ethylene group, a trimethylene group, atetramethylene group, a propylene group, an ethylethylene group, apentamethylene group, a hexamethylene group, a2,2,4-trimethylhexamethylene group, a heptamethylene group, anoctamethylene group, a nonamethylene group, a decamethylene group, anundecamethylene group, a dodecamethylene group, a cyclohexylene group(for example, a 1,6-cyclohexanediyl group and the like), acyclopentylene group (for example, 1,5-cyclopentanediyl group and thelike), and the like), an alkenylene group (for example, a vinylenegroup, a propenylene group and the like), an alkynylene group (forexample, an ethynylene group, a 3-pentenylene group and the like) and anarylene group, and the like.

Further, in each of the above-described alkylene group, alkenylenegroup, alkynylene group and arylene group, at least one of carbon atoms,which constitute a divalent linking group, may be substituted with achalcogen atom (such as oxygen, sulfur and the like) or said —N(R)—group, and the like.

In addition, as a divalent linking group represented by L₁, for example,a group having a divalent heterocyclic group is used, and examplesthereof include an oxazolediyl group, a pyrimidinediyl group, apyridazinediyl group, a pyrandiyl group, a pyrrolinediyl group, animidazolinediyl group, an imidazolidinediyl group, a pyrazolidinediylgroup, a pyrazolinediyl group, a piperidinediyl group, a piperazinediylgroup, a morpholinediyl group, a quinuclidinediyl group and the like,and may also be a divalent linking group derived from a compound havingan aromatic heterocyclic ring (also referred to as a heteroaromaticcompound) such as a thiophene-2,5-diyl group or a pyrazine-2,3-diylgroup.

Furthermore, linking groups through a heteroatom, such as an alkyliminogroup, a dialkylsilanediyl group and a diarylgermanediyl group may beused.

The divalent linking group represented by L₁ includes preferably amethylene group, an ethylene group, a cyclohexylene group, acyclopentylene group, a substituted silicon atom, a substitutedgermanium atom, an oxygen atom, a sulfur atom, a 5- or 6-memberedaromatic hydrocarbon ring group and an aromatic heterocyclic group, morepreferably a methylene group, an ethylene group, a cyclohexylene group,a substituted or unsubstituted nitrogen atom, a substituted siliconatom, a substituted germanium atom, a 5- or 6-membered aromatichydrocarbon ring group, even more preferably a methylene group, anethylene group, a substituted silicon atom, a substituted nitrogen atom,and a substituted germanium atom, particularly preferably a methylenegroup substituted with an alkyl group or a phenyl group, a silicon atom,a germanium atom, and a nitrogen atom, and most preferably a methylenegroup substituted with an alkyl group or a phenyl group and a siliconatom.

These linking groups may further have a substituent, if possible, and asa substituent which may be introduced, those exemplified for the group Aof substituents may be applied. When an aromatic hydrocarbon ring groupor aromatic heterocyclic group is used as the linking group, the size ofthe ring is a 5- or 6-membered ring.

In the above Formula, each of R₉₁ to R₉₁₀ independently represents ahydrogen atom, a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group, afluorine atom or a group represented by any one of Formula (10), (10-2)or (10-3) as described below, but it is preferred that each of at leasttwo of R₉₁ to R₉₁₀ is independently a group represented by any one ofFormula (10), (10-2) or (10-3) as described below, L₁ represents asilicon atom or a carbon atom, and the silicon atom or carbon atom maybe further substituted with at least one group selected from an alkylgroup and an aryl group.

In Formulas (3) to (9), one of the preferable forms is that thesubstituent represented by Formula (3a-1) is a compound represented bythe following Formula (10).

(wherein R₁₀₂ represents hydrogen and a substituted or unsubstitutedaromatic hydrocarbon group or aromatic heterocyclic group, which is nota condensed ring structure, and each of R₁₀₁ and R₁₀₃ independentlyrepresents a hydrogen atom or a substituent. R₁₀₄ represents asubstituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group, which is not a condensed ring structure other than anaphthalene ring.)

Each of R₁₀₁ and R₁₀₃ independently represents a hydrogen atom or asubstituent, and has the same meaning as R₃₁ and R₃₂ in Formula (3a-1),and preferred ranges thereof are also the same.

R₁₀₄ represents a substituted or unsubstituted aromatic hydrocarbongroup or aromatic heterocyclic group, which is not a condensed ringstructure other than a naphthalene ring, and has the same meaning as R₃₄in Formula (3c), and preferred ranges thereof are also the same.

A substituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group, which is not a condensed ring structure, representedby R₁₀₂, may include a benzene ring, a biphenyl ring, an o-terphenylring, an m-terphenyl ring, a p-terphenyl group, a furan ring, athiophene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, apyrazine ring, an oxadiazole ring, a triazole ring, an imidazole ring, apyrazole ring, a thiazole ring and the like. The aromatic heterocyclicring may have a substituent, and as the substituent, those exemplifiedabove for the group A of substituents may be applied.

R₁₀₂ includes preferably a hydrogen atom, a benzene ring, a biphenylring, a pyrazole ring, an imidazole ring, a triazole ring, a pyridinering, and a thiophene ring, more preferably a hydrogen atom, a benzenering, a biphenyl ring and a pyridine ring, and particularly preferably ahydrogen atom.

R₁₀₂ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied, andmay include preferably alkyl having 1 to 6 carbon atoms, phenyl, pyridyland the like.

In Formulas (3) to (10) and Formulas (3a-1) to (3h), it is preferredthat the ring A and the ring C are a benzene ring, R₃₄, R₃₉, R₃₁₀ andR₁₀₄ are a substituted or unsubstituted phenyl group or pyridyl group,and further, R₃₁ to R₃₂, R₃₅ to R₃₇, and R₁₀₁ to R₁₀₃ are a hydrogenatom or a phenyl group.

Further, in Formulas (3) to (9), it is also preferred that thesubstituent represented by Formula (3a-1) is a compound represented bythe following Formula (10-2).

(wherein R₁₀₂ represents hydrogen and a substituted or unsubstitutedaromatic hydrocarbon group or aromatic heterocyclic group which is not acondensed ring structure, and each of R₁₀₁ and R₁₀₃ independentlyrepresents a hydrogen atom or a substituent. R₁₀₄ represents asubstituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group, which is not a condensed ring structure other than anaphthalene ring.)

Each of R₁₀₁ and R₁₀₃ independently represents a hydrogen atom or asubstituent, and has the same meaning as R₃₁ and R₃₂ in Formula (3a-1),and preferred ranges thereof are also the same.

R₁₀₄ represents a substituted or unsubstituted aromatic hydrocarbongroup or aromatic heterocyclic group, which is not a condensed ringstructure other than a naphthalene ring, and has the same meaning as R₃₄in Formula (3c), and preferred ranges thereof are also the same.

The substituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group represented by R₁₀₂, which is not a condensed ringstructure, is the same as R₁₀₂ in Formula (10).

R₁₀₂ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied, andmay include preferably alkyl having 1 to 6 carbon atoms, phenyl, pyridyland the like.

Further, in Formulas (3) to (9), it is also preferred that thesubstituent represented by Formula (3a-1) is a compound represented bythe following Formula (10-3).

(wherein R₁₀₂ represents hydrogen and a substituted or unsubstitutedaromatic hydrocarbon group or aromatic heterocyclic group which is not acondensed ring structure, and each of R₁₀₁ and R₁₀₃ independentlyrepresents a hydrogen atom or a substituent. R₁₀₄ represents asubstituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group, which is not a condensed ring structure other than anaphthalene ring.)

Each of R₁₀₁ and R₁₀₃ independently represents a hydrogen atom or asubstituent, and has the same meaning as R₃₁ and R₃₂ in Formula (3a-1),and preferred ranges thereof are also the same.

R₁₀₄ represents a substituted or unsubstituted aromatic hydrocarbongroup or aromatic heterocyclic group, which is not a condensed ringstructure other than a naphthalene ring, and has the same meaning as R₃₄in Formula (3c), and preferred ranges thereof are also the same.

The substituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group represented by R₁₀₂, which is not a condensed ringstructure is the same as R₁₀₂ in Formula (10).

R₁₀₂ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied, andmay include preferably alkyl having 1 to 6 carbon atoms, phenyl, pyridyland the like.

In Formulas (10-2) and (10-3), it is preferred that R₁₀₄ is asubstituted or unsubstituted phenyl group or pyridyl group and R₁₀₁ toR₁₀₃ are a hydrogen atom or a phenyl group.

In Formulas (10), (10-2) and (10-3), it is preferred that R₁₀₂represents a hydrogen atom, each of R₁₀₁ and R₁₀₃ independentlyrepresents a hydrogen atom, an alkyl group, a silyl group, a fluorineatom, a cyano group or a trifluoromethyl group, these groups may befurther substituted with at least one of an alkyl group having 1 to 6carbon atoms and a phenyl group, R₁₀₄ represents a benzene ring, anaphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring,and these rings may be further substituted with at least one selectedfrom a methyl group, an isobutyl group, a t-butyl group, a neopentylgroup, a phenyl group, a naphthyl group, a cyano group and a fluorineatom.

Among Formulas (10), (10-2) and (10-3), Formula (10) is particularlypreferable.

As the compound represented by Formula (3), one of the preferable formsis a compound represented by the following Formula (11).

(wherein each of R₁₁₁ to R₁₁₆ independently represents a hydrogen atomor a substituent. However, at least one of R₁₁₁ to R₁₁₅ is a grouprepresented by Formula (3a-1), (3a-2) or (3e). m represents an integerof 1 to 4.)

Each of R₁₁₁ to R₁₁₅ independently represents a hydrogen atom or asubstituent, and as the substituent, those exemplified above for thegroup A of substituents may be applied.

At least one of R₁₁₁ to R₁₁₅ is a group represented by Formula (3a-1),(3a-2) or (3e), and preferably a group represented by Formula (10).

R₁₁₁ and R₁₁₅ preferably include a hydrogen atom, an alkyl group, analicyclic hydrocarbon group, an aryl group, a fluorine group, an aminogroup, an alkoxy group, an aryloxy group, a heterocyclic oxy group, analkylthio group, an arylthio group, a heterocyclic thio group, a cyanogroup, a heterocyclic group, a silyl group and a silyloxy group, morepreferably a hydrogen atom, an alkyl group, an alicyclic hydrocarbongroup, an aryl group, a fluorine group, a cyano group, a silyl group anda heterocyclic group, even more preferably a hydrogen atom, an alkylgroup, an alicyclic hydrocarbon group, an aryl group, a fluorine group,a cyano group, a silyl group and a heterocyclic group, and particularlypreferably a hydrogen atom, an alkyl group, an alicyclic hydrocarbongroup, an aryl group and a heterocyclic group.

In R₁₁₁ to R₁₁₅, R₁₁₃ is particularly preferably a group represented byFormula (3a-1).

R₁₁₁ to R₁₁₅ may further have a substituent, and as the substituent,those exemplified above for the group A of substituents may be applied.Further, a plurality of substituents may be linked to each other to forma ring.

R₁₁₆ represents a hydrogen atom or a substituent. Each R₁₁₆ may be thesame as or different from every other R₁₁₆.

As the substituent represented by R₁₁₆, those exemplified above for thegroup A of substituents may be applied.

R₁₁₆ includes preferably a hydrogen atom, an alkyl group, an aromatichydrocarbon ring group, an amino group, an alkoxy group, an aryloxygroup, an aromatic heterocyclic oxy group, an alkylthio group, anarylthio group, a heterocyclic thio group, a cyano group, an aromaticheterocyclic group, a silyl group and a silyloxy group, more preferablyan alkyl group, an aromatic hydrocarbon ring group, an amino group, acyano group and an aromatic heterocyclic group, even more preferably analkyl group, an aromatic hydrocarbon ring group, a cyano group and anaromatic heterocyclic group, and particularly preferably an alkyl groupand an aromatic hydrocarbon ring group.

m represents an integer of 1 to 4, preferably 1 to 3, and morepreferably 2.

In the above Formula, each of R₁₁₁ to R₁₁₆ independently represents ahydrogen atom, a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group, afluorine atom or a group represented by any one of Formula (10), (10-2)or (10-3) as described above, but it is preferred that at least one ofR₁₁₁ to R₁₁₅ is a group represented by any one of Formula (10), (10-2)or (10-3) as described above, and m represents an integer of 1 to 4.

As the compound represented by Formula (3), one of the preferable formsis a compound represented by the following Formula (12).

(wherein each of R₁₂₁ to R₁₂₆ independently represents a hydrogen atomor a substituent. However, at least one of R₁₂₁ to R₁₂₅ is a grouprepresented by Formula (3a-1), (3a-2) or (3e). m represents an integerof 1 to 4.)

Each of R₁₂₁ to R₁₂₅ independently represents a hydrogen atom of asubstituent, and as the substituent, those exemplified above for thegroup A of substituents may be applied. At least one of R₁₂₁ to R₁₂₅ isa group represented by Formula (3a-1), (3a-2) or (3e), and preferably agroup represented by Formula (10).

R₁₂₁ and R₁₂₅ preferably include a hydrogen atom, an alkyl group, analicyclic hydrocarbon group, an aryl group, a fluorine group, an aminogroup, an alkoxy group, an aryloxy group, a heterocyclic oxy group, analkylthio group, an arylthio group, a heterocyclic thio group, a cyanogroup, a heterocyclic group, a silyl group and a silyloxy group, morepreferably a hydrogen atom, an alkyl group, an alicyclic hydrocarbongroup, an aryl group, a fluorine group, a cyano group, a silyl group anda heterocyclic group, even more preferably a hydrogen atom, an alkylgroup, an alicyclic hydrocarbon group, an aryl group, a fluorine group,a cyano group, a silyl group and a heterocyclic group, and particularlypreferably a hydrogen atom, an alkyl group, an alicyclic hydrocarbongroup, an aryl group and a heterocyclic group.

R₁₂₁ to R₁₂₅ may further have a substituent, and as the substituent,those exemplified above for the group A of substituents may be applied.Further, a plurality of substituents may be linked to each other to forma ring.

R₁₂₆ represents a hydrogen atom or a substituent. Each R₁₂₆ may be thesame as or different from every other R₁₂₆.

As the substituent represented by R₁₂₆, those exemplified above for thegroup A of substituents may be applied.

R₁₂₆ includes preferably a hydrogen atom, an alkyl group, an aromatichydrocarbon ring group, an amino group, an alkoxy group, an aryloxygroup, an aromatic heterocyclic oxy group, an alkylthio group, anarylthio group, a heterocyclic thio group, a cyano group, an aromaticheterocyclic group, a silyl group and a silyloxy group, more preferablyan alkyl group, an aromatic hydrocarbon ring group, an amino group, acyano group and an aromatic heterocyclic group, even more preferably analkyl group, an aromatic hydrocarbon ring group, a cyano group and anaromatic heterocyclic group, and particularly preferably an alkyl groupand an aromatic hydrocarbon ring group.

m represents an integer of 1 to 4, preferably 1 to 3, and morepreferably 2.

In the above Formula, each of R₁₂₁ to R₁₂₆ independently represents ahydrogen atom, a methyl group, an isobutyl group, a t-butyl group, aneopentyl group, a phenyl group, a naphthyl group, a cyano group, afluorine atom or a group represented by any one of Formula (10), (10-2)or (10-3) as described above, but it is preferred that at least one ofR₁₂₁ to R₁₂₅ is a group represented by any one of Formula (10), (10-2)or (10-3) as described above and m represents an integer of 1 to 4.

As the compound represented by Formula (1), one of preferable forms is acompound represented by the following Formula (13).

(R₁₃₂ represents hydrogen or a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group which is not acondensed ring structure, and each of R₁₃₁ and R₁₃₃ independentlyrepresents a hydrogen atom or a substituent. R₁₃₄ and R₁₃₅ represent asubstituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group, which is not a condensed ring structure other than anaphthalene ring. R₁₃₆ represents a hydrogen atom or a substituent. mrepresents an integer of 1 to 4. A silicon linking group as R₁₃₁ issubstituted to a carbon atom.)

Each of R₁₃₁ and R₁₃₃ independently represents a hydrogen atom or asubstituent, and has the same meaning as R₁₂ and R₁₃ in Formula (1), andpreferred ranges thereof are also the same.

R₁₃₄ and R₁₃₅ represent a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group, which is not acondensed ring structure other than a naphthalene ring, and has the samemeaning as R₁₁ and R₁₅ in Formula (1), and preferred ranges thereof arealso the same.

A substituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group represented by R₁₃₂, which is not a condensed ringstructure, may include a benzene ring, a biphenyl ring, an o-terphenylring, an m-terphenyl ring, a p-terphenyl ring, a furan ring, a thiophenering, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazinering, an oxadiazole ring, a triazole ring, an imidazole ring, a pyrazolering, a thiazole ring and the like. The aromatic heterocyclic ring mayhave a substituent, and as the substituent, those exemplified above forthe group A of substituents may be applied.

R₁₃₂ includes preferably a hydrogen atom, a benzene ring, a biphenylring, a pyrazole ring, an imidazole ring, a triazole ring, a pyridinering and a thiophene ring, more preferably a hydrogen atom, a benzenering, a biphenyl ring and a pyridine ring, and particularly preferably ahydrogen atom.

R₁₃₂ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied, andmay include preferably alkyl having 1 to 6 carbon atoms, phenyl, pyridyland the like.

R₁₃₆ represents a hydrogen atom or a substituent. Each R₁₃₆ may be thesame as or different from every other R₁₃₆.

As the substituent represented by R₁₃₆, those exemplified above for thegroup A of substituents may be applied.

R₁₃₆ includes preferably a hydrogen atom, an alkyl group, an aromatichydrocarbon ring group, an amino group, an alkoxy group, an aryloxygroup, an aromatic heterocyclic oxy group, an alkylthio group, anarylthio group, a heterocyclic thio group; a cyano group, an aromaticheterocyclic group, a silyl group and a silyloxy group, more preferablyan alkyl group, an aromatic hydrocarbon ring group, an amino group, acyano group and an aromatic heterocyclic group, even more preferably, analkyl group, an aromatic hydrocarbon ring group, a cyano group and anaromatic heterocyclic group, and particularly preferably an alkyl groupand an aromatic hydrocarbon ring group.

m represents an integer of 1 to 4, preferably 1 to 3, and morepreferably 2.

In the above Formula, it is preferred that R₁₃₂ represents a hydrogenatom, each of R₁₃₁ and R₁₃₃ independently represents a hydrogen atom, analkyl group, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, these groups may be further substituted with atleast one of an alkyl group having 1 to 6 carbon atoms and a phenylgroup, each of R₁₃₄ and R₁₃₅ independently represents a benzene ring; anaphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring,these rings may be further substituted with at least one group selectedfrom a methyl group, an isobutyl group, a t-butyl group, a neopentylgroup, a phenyl group, a naphthyl group, a cyano group and a fluorineatom, R₁₃₆ represents a hydrogen atom, a methyl group, an isobutylgroup, a t-butyl group, a neopentyl group, a phenyl group, a naphthylgroup, a cyano group or a fluorine atom, m represents an integer of 1 to4, and a silicon linking group as one of R₁₃₁ is substituted to a carbonatom.

As the compound represented by Formula (1), one of preferable forms is acompound represented by the following Formula (14).

(wherein R₁₄₂ represents hydrogen or a substituted or unsubstitutedaromatic hydrocarbon group or aromatic heterocyclic group, which is nota condensed ring structure, each of R₁₄₁ and R₁₄₃ independentlyrepresents a hydrogen atom or a substituent, and R₁₄₄ and R₁₄₅ representa substituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group, which is not a condensed ring structure other than anaphthalene ring. A carbon linking group as R₁₄₁ is substituted to acarbon atom. R₁₄₆ represents a hydrogen atom or a substituent. mrepresents an integer of 1 to 4.)

Each of R₁₄₁ and R₁₄₃ independently represents a hydrogen atom or asubstituent, and has the same meaning as R₁₂ and R₁₃ in Formula (1), andpreferred ranges thereof are also the same.

R₁₄₄ and R₁₄₅ represent a substituted or unsubstituted aromatichydrocarbon group or aromatic heterocyclic group, which is not acondensed ring structure other than a naphthalene ring, and has the samemeaning as R₁₁ and R₁₅ in Formula (1), and preferred ranges thereof arealso the same.

A substituted or unsubstituted aromatic hydrocarbon group or aromaticheterocyclic group represented by R₁₄₂, which is not a condensed ringstructure may include a benzene ring, a biphenyl ring, an o-terphenylring, an m-terphenyl ring, a p-terphenyl ring, a furan ring, a thiophenering, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazinering, an oxadiazole ring, a triazole ring, an imidazole ring, a pyrazolering, a thiazole ring and the like. The aromatic heterocyclic ring mayhave a substituent, and as the substituent, those exemplified above forthe group A of substituents may be applied.

R₁₄₂ includes preferably a hydrogen atom, a benzene ring, a biphenylring, a pyrazole ring, an imidazole ring, a triazole ring, a pyridinering and a thiophene ring, more preferably a hydrogen atom, a benzenering, a biphenyl ring and a pyridine ring, and particularly preferably ahydrogen atom.

R₁₄₂ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied, andmay include preferably alkyl having 1 to 6 carbon atoms, phenyl, pyridyland the like.

R₁₄₆ represents a hydrogen atom or a substituent. Each R₁₄₆ may be thesame as or different from every other R₁₄₆.

As the substituent represented by R₁₄₆, those exemplified above for thegroup A of substituents may be applied.

R₁₄₆ includes preferably a hydrogen atom, an alkyl group, an aromatichydrocarbon ring group, an amino group, an alkoxy group, an aryloxygroup, an aromatic heterocyclic oxy group, an alkylthio group, anarylthio group, a heterocyclic thio group, a cyano group, an aromaticheterocyclic group, a silyl group and a silyloxy group, more preferablyan alkyl group, an aromatic hydrocarbon ring group, an amino group, acyano group and an aromatic heterocyclic group, even more preferably analkyl group, an aromatic hydrocarbon ring group, a cyano group and anaromatic heterocyclic group, and even more preferably an alkyl group andan aromatic hydrocarbon ring group.

m represents an integer of 1 to 4, preferably 1 to 3, and morepreferably 2.

In the above Formula, it is preferred that R₁₄₂ represents a hydrogenatom, each of R₁₄₁ and R₁₄₃ independently represents a hydrogen atom, analkyl group, a silyl group, a fluorine atom, a cyano group or atrifluoromethyl group, these groups may be substituted with at least oneof an alkyl group having 1 to 6 carbon atoms and a phenyl group, each ofR₁₄₄ and R₁₄₅ independently represents a benzene ring, a naphthalenering, a pyridine ring, a triazine ring or a pyrimidine ring, these ringsmay be further substituted with at least one group selected from amethyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group and a fluorine atom, acarbon linking group is substituted to a carbon atom as one of R₁₄₁,R₁₄₆ represents a hydrogen atom, a methyl group, an isobutyl group, at-butyl group, a neopentyl group, a phenyl group, a naphthyl group, acyano group or a fluorine atom, and m represents an integer of 1 to 4.

Preferred specific examples of the compounds represented by Formulas (1)to (18) are represented below, but are not limited thereto.

Compound Central Skeleton A 148

149

150

151

152

153

154

155

156

157

158

159

160

161

162

163

164

165

166

167

168

169

170

171

172

173

174

175

176

177

178

179

180

181

182

183

184

185

186

187

188

189

190

191

192

193

194

195

The compound represented by Formula (1) may be easily prepared bymethods known in the art. For example, preparation may be performed withreference to Synthetic Examples shown in Tetrahedron, 47, 7739-7750(1991), Synlett, 42-48 (2005).

In the present invention, the compound represented by Formula (1) isincluded in a light emitting layer from the viewpoint of improving lightemission efficiency and durability (in particular, durability whendriving at a high temperature), but the use thereof is not limited andmay be included in any layer in addition to the light emitting layerwithin the organic layer. It is preferred that as a layer whichintroduces the compound represented by Formula (1), the compound isincluded in one of a hole injection layer, a hole transporting layer, anelectron transporting layer, an electron injection layer, an excitonblocking layer and a charge blocking layer, or a plurality thereof inaddition to a light emitting layer.

Further, the compound represented by Formula (1) may be contained inboth layers of the light emitting layer and the layer adjacent to thelight emitting layer.

[Compound represented by Formula (D-1)]

A compound represented by Formula (D-1) will be described in detail.

(In Formula (D-1), M represents a metal having an atomic weight of 40 ormore. Each of R₃ to R₆ independently represents a hydrogen atom or asubstituent. R₃′ represents a hydrogen atom or a substituent. The ring Qrepresents a pyridine ring, a quinoline ring or an isoquinoline ring,which is coordinated to the metal M, and may be further substituted witha non-aromatic group. R₅ represents an aryl group or a heteroaryl groupwhen the ring Q is a pyridine ring. R₃′ and R₆ may be linked to eachother by a linking group selected from —CR₂—CR₂—, CR═CR—, —CR₂—, —O—,—NR—, —O—CR₂—, —NR—CR₂— and —N═CR— to form a ring, each R independentlyrepresents a hydrogen atom, an alkyl group, an alkenyl group, an alkynylgroup, a heteroalkyl group, an aryl group or a heteroaryl group, and mayfurther have a substituent selected from a halogen atom, —R′, —OR′,—N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)₂, —CN, —NO₂, —SO₂, —SOR′,—SO₂R′ and —SO₃R′, and each R′ independently represents a hydrogen atom,an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynylgroup, a heteroalkyl group, an aryl group or a heteroaryl group. (X—Y)represents an ancillary ligand. m represents a value of 1 to thegreatest number of ligands that may be bound to the metal, and nrepresents a value of 0 to the greatest number of ligands that may bebound to the metal. m+n is the greatest number of ligands that may bebound to the metal.)

In Formula (D-1), M represents a metal having an atomic weight of 40 ormore, and may include Ir, Pt, Cu, Re, W, Rh, Ru, Pd, Os, Eu, Tb, Gd, Dyand Ce. Preferably, M is Ir, Pt or Re, and among them, Ir, Pt or Re,which may form a coordination mode of a metal-carbon bond or ametal-nitrogen bond, is preferable, and Ir is particularly preferablefrom the viewpoint of high light emission quantum efficiency.

Each of R₃ to R₆ and R₃′ independently represents a hydrogen atom or asubstituent. As the substituent represented by R₃ to R₆ and R₃′, thoseexemplified above for the group A of substituents may be applied.

The aryl group represented by R₃ to R₆ and R₃′ may include preferably asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, forexample, a phenyl group, a tolyl group, a naphthyl group, and the like.

The heteroaryl group represented by R₃ to R₆ and R₃′ may includepreferably a heteroaryl group having 5 to 8 carbon atoms, morepreferably a 5- or 6-membered, substituted or unsubstituted heteroarylgroup, for example, a pyridyl group, a pyrazinyl group, a pyridazinylgroup, a pyrimidinyl group, a triazinyl group, a quinolinyl group, anisoquinolinyl group, a quinazolinyl group, a cinnolinyl group, aphthalazinyl group, a quinoxalinyl group, a pyrrolyl group, an indolylgroup, a furyl group, a benzofuryl group, a thienyl group, abenzothienyl group, a pyrazolyl group, an imidazolyl group, abenzimidazolyl group, a triazolyl group, an oxazolyl group, abenzoxazolyl group, a thiazolyl group, a benzothiazolyl group, anisothiazolyl group, a benzisothiazolyl group, a thiadiazolyl group, anisoxazolyl group, a benzisoxazolyl group, a pyrrolidinyl group, apiperidinyl group, a piperazinyl group, an imidazolidinyl group, athiazolinyl group, a sulfolanyl group and the like.

Preferable examples of the heterocyclic group represented by R₃′ includea pyridyl group, a pyrimidinyl group, an imidazolyl group, a thienylgroup, and more preferably a pyridiyl group and a pyrimidinyl group.

R₃′ includes preferably a hydrogen atom, an alkyl group, a cyano group,a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, afluoro group, an aryl group and a heteroaryl group, more preferably ahydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, afluoro group and an aryl group, and even more preferably a hydrogenatom, an alkyl group and aryl group.

R₃, R₄, and R₆ include preferably a hydrogen atom, an alkyl group, acycloalkyl group, a cyano group, a perfluoroalkyl group, a dialkylaminogroup, a fluoro group, an aryl group and a heteroaryl group, morepreferably a hydrogen atom, an alkyl group, a cyano group, atrifluoromethyl group, a fluoro group and an aryl group, and even morepreferably a hydrogen atom, an alkyl group and an aryl group.

Further, R₃ to R₆ and R₃′ may further have a substituent, and as thesubstituent, those exemplified above for the group A of substituents maybe applied. The substituent includes an alkyl group, an aryl group, acyano group, a halogen atom and a nitrogen-containing aromaticheterocyclic group, and more preferably alkyl having 1 to 6 carbonatoms, an aryl group having 6 to 10 carbon atoms, pyridyl, a fluorineatom and a cyano group, and even more preferably an alkyl group having 1to 6 carbon atoms, a phenyl group and a cyano group. in addition, R₃ toR₆ may be linked to each other to form a condensed ring, and a ring tobe formed may include a benzene ring, a pyridine ring, a pyrazine ring,a pyrimidine ring, a triazine ring, a pyridazine ring, a pyrrole ring, apyrazole ring, an imidazole ring, a triazole ring, an oxazole ring, anoxadiazole ring, a thiazole ring, a thiadiazole ring, a furan ring, athiophene ring, a selenophene ring, a silole ring, a germole ring, aphosphole ring, a carbazole ring and the like.

R₅ becomes an aryl group or a heteroaryl group when the ring Q is apyridine ring. The aryl group or heteroaryl group may further have asubstituent, and the substituent includes preferably an alkyl group, acyano group, a perfluoroalkyl group, a dialkylamino group, a fluorogroup, an aryl group and a heteroaryl group, and more preferably ahydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, afluoro group and an aryl group, and even more preferably a hydrogenatom, an alkyl group, a cyano group and an aryl group.

R₅ includes preferably a phenyl group, a p-tolyl group and a naphthylgroup, and more preferably a phenyl group.

When the ring Q is a quinoline ring or an isoquinoline ring, R₅ includespreferably an alkyl group, an alkoxy group, a fluoro group, a cyanogroup, an alkylamino group and a diarylamino group, more preferably analkyl group, a fluoro group and a cyano group, even more preferably analkyl group, and particularly preferably a methyl group. Further, whenthe ring Q is a quinoline ring or an isoquinoline ring and R₅ is analkyl group, R₃ is also preferably an alkyl group, and more preferably amethyl group.

The ring Q represents a pyridine ring, a quinoline ring or anisoquinoline ring, which is coordinated to the metal M, and may befurther substituted with a substituent. The substituent includes analkyl group, an aryl group, a cyano group, a perfluoroalkyl group, adialkylamino group, a fluoro group, a pyridyl group, a thienyl group andan alkoxy group, more preferably an alkyl group, an aryl group, analkoxy group, a cyano group, a dialkylamino group, a fluoro group, apyridyl group and a thienyl group, even more preferably an alkyl groupand an aryl group, and particularly preferably an alkyl group.

It is preferred that the ring Q does not further have theabove-mentioned substituent or is substituted with an alkyl group or anaryl group, and it is more preferred that the ring Q has no furthersubstituent or is substituted with an alkyl group.

m is preferably 1 to 6, and more preferably 1 to 3. When M is Ir, m ispreferably 1 to 3, and more preferably 2. n is preferably 0 to 3, andmore preferably 0 to 1. When M is Ir, n is preferably 1 to 3. It is morepreferable that m is 2 and n is 1.

(X—Y) represents a bidendate ligand. The bidendate ligand represented by(X—Y) is not particularly limited, but specific examples thereofinclude, for example, substituted or unsubstituted phenylpyridine,phenylpyrazole, phenylimidazole, phenyltriazole, phenyltetrazole,pyridylpyridine, imidazolylpyridine, pyrazolylpyridine,triazolylpyridine, pyrazabole, diphenylphosphinoethylene, picolinicacid, acetylacetone and the like. Among them, phenylpyridine,phenylpyrazole, phenyl imidazole, pyridylpyridine, pyrazabole, picolinicacid, acetylacetone and the like are preferable, and phenylpyridine,picolinic acid and acetylacetone are more preferable.

Further, specific examples of the bidendate ligand represented by (X—Y)include a ligand represented by any one of the following Formulas (1-1)to (1-15).

In the above Formula, * represents a coordination position as a metal.

Each of Rx, Ry and Rz independently represents a hydrogen atom or asubstituent. The substituent may include a substituent selected from thegroup A of substituents.

Rx and Rz are preferably any one of an alkyl group, a perfluoroalkylgroup, a halogen atom and an aryl group, and more preferably an alkylgroup.

Ry is preferably one of a hydrogen atom, an alkyl group, aperfluoroalkyl group, a halogen atom, and an aryl group, and morepreferably a hydrogen atom or an alkyl group.

In Formulas (1-1) to (1-14), Formula (1-1), (1-4) or (1-15) is morepreferable.

One of the preferable forms of the compound represented by Formula (D-1)is a compound represented by the following Formula (D-2).

(In Formula (D-2), M represents a metal having an atomic weight of 40 ormore. Each of R₃ to R₆ independently represents a hydrogen atom or asubstituent. Each of R₃ to R₈ independently represents a hydrogen atomor a substituent. R₃′ and R₆ may be linked to each other by a linkinggroup selected from —CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —O—CR₂—,—NR—CR₂— and —N═CR— to form a ring, and each R independently representsa hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, aheteroalkyl group, an aryl group or a heteroaryl group, and may furtherhave a substituent Z. Each Z independently represents a halogen atom,—R′, —OR′, —N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)₂, —CN, —NO₂,—SO₂, —SOR′, —SO₂R′ or —SO₃R′, and each R′ represents a hydrogen atom,an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynylgroup, a heteroalkyl group, an aryl group or a heteroaryl group. (X—Y)represents an ancillary ligand. m represents a value of 1 to thegreatest number of ligands that may be bound to the metal, and nrepresents a value of 0 to the greatest number of ligands that may bebound to the metal. m+n is the greatest number of ligands that may bebound to the metal.)

M, R₃′, m and n in Formula (D-2) have the same meaning as M, R₃′, m andn in Formula (D-1), and preferred ranges thereof are also the same.

Each of R₃ to R₆ independently represents a hydrogen atom or asubstituent. As the substituent represented by R₃ to R₆, thoseexemplified above for the group A of substituents may be applied.

R₃ to R₆ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied. Thesubstituent includes an alkyl group, an aryl group, a cyano group, ahalogen atom and a nitrogen-containing aromatic heterocyclic group, andmore preferably alkyl having 1 to 6 carbon atoms, an aryl group having 6to 10 carbon atoms, pyridyl, a fluorine atom and a cyano group, and evenmore preferably an alkyl group having 1 to 6 carbon atoms, a phenylgroup and a cyano group. Further, R₃ to R₆ may be linked to each otherto form a condensed ring, and a ring to be formed may include a benzenering, a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazinering, a pyridazine ring, a pyrrole ring, a pyrazole ring, an imidazolering, a triazole ring, an oxazole ring, an oxadiazole ring, a thiazolering, a thiadiazole ring, a furan ring, a thiophene ring, a selenophenering, a silole ring, a germole ring, a phosphole ring and the like.

The aryl group represented by R₃ to R₆ may include preferably asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, forexample, a phenyl group, a tolyl group, a naphthyl group and the like.

The heteroaryl group represented by R₃ to R₆ may include preferably aheteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or6-membered, substituted or unsubstituted heteroaryl group, for example,a pyridyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinazolinyl group, a cinnolinyl group, a phthalazinyl group, aquinoxalinyl group, a pyrrolyl group, an indolyl group, a furyl group, abenzofuryl group, a thienyl group, a benzothienyl group, a pyrazolylgroup, an imidazolyl group, a benzimidazolyl group, a triazolyl group,an oxazolyl group, a benzoxazolyl group, a thiazolyl group, abenzothiazolyl group, an isothiazolyl group, a benzisothiazolyl group, athiadiazolyl group, an isoxazolyl group, a benzisoxazolyl group, apyrrolidinyl group, a piperidinyl group, a piperazinyl group, animidazolidinyl group, a thiazolinyl group, a sulfolanyl group and thelike.

R₃ to R₆ include preferably a hydrogen atom, an alkyl group, a cyanogroup, a trifluoromethyl group, a perfluoroalkyl group, a dialkylaminogroup, a fluoro group, an aryl group and a heteroaryl group, morepreferably a hydrogen atom, an alkyl group, a cyano group, atrifluoromethyl group, a fluoro group and an aryl group, and even morepreferably a hydrogen atom, an alkyl group and an aryl group. Inparticular, R₃ and R₅ include preferably an alkyl group, more preferablyan ethyl group, an isobutyl group, a t-butyl group, a neopentyl groupand a methyl group, particularly preferably an ethyl group, an isobutylgroup, a neopentyl group and a methyl group, and even more preferably amethyl group.

Each of R₄′ to R₈′ independently represents a hydrogen atom or asubstituent. As the substituent represented by R₄′ to R₈′, thoseexemplified above for the group A of substituents may be applied.

The aryl group represented by R₄′ to R₈′ may include preferably asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, forexample, a phenyl group, a tolyl group, a naphthyl group and the like.

The heteroaryl group represented by R₄′ to R₈′ may include preferably aheteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or6-membered, substituted or unsubstituted heteroaryl group, for example,a pyridyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinazolinyl group, a cinnolinyl group, a phthalazinyl group, aquinoxalinyl group, a pyrrolyl group, an indolyl group, a furyl group, abenzofuryl group, a thienyl group, a benzothienyl group, a pyrazolylgroup, an imidazolyl group, a benzimidazolyl group, a triazolyl group,an oxazolyl group, a benzoxazolyl group, a thiazolyl group, abenzothiazolyl group, an isothiazolyl group, a benzisothiazolyl group, athiadiazolyl group, an isoxazolyl group, a benzisoxazolyl group, apyrrolidinyl group, a piperidinyl group, a piperazinyl group, animidazolidinyl group, a thiazolinyl group, a sulfolanyl group and thelike.

R₄′ to R₈′ includes preferably a hydrogen atom, an alkyl group, a cyanogroup, a trifluoromethyl group, a perfluoroalkyl group, a dialkylaminogroup, a fluoro group, an aryl group, a heteroaryl group and an alkoxygroup, more preferably a hydrogen atom, an alkyl group, a cyano group, atrifluoromethyl group, a fluoro group, an aryl group, an alkoxy groupand a thienyl group, and even more preferably a hydrogen atom, an alkylgroup and an aryl group, and particularly preferably a hydrogen atom andan alkyl group.

Further, R₄′ to R₈′ may further have a substituent, and as thesubstituent, those exemplified above for the group A of substituents maybe applied. The substituent includes preferably an alkyl group, an arylgroup, a cyano group, a halogen atom and a nitrogen-containing aromaticheterocyclic group, and more preferably alkyl having 1 to 6 carbonatoms, an aryl group having 6 to 10 carbon atoms, pyridyl, a cyano groupand a halogen atom, even more preferably a branched alkyl group having 3to 6 carbon atoms, a phenyl group, a naphthyl group, a cyano group and afluorine atom, and particularly preferably an isobutyl group, a t-butylgroup, a neopentyl group, a phenyl group, a naphthyl group, a cyanogroup and a fluorine atom. The number of substituents is 0 to 4, andpreferably 0 to 2. Further, a plurality of substituents may be linked toeach other to form a ring.

In addition, R₄′ to R₈′ may be linked to each other to form a condensedring, and a ring to be formed may include a benzene ring, a pyridinering, a pyrazine ring, a pyrimidine ring, a triazine ring, a pyridazinering, a pyrrole ring, a pyrazole ring, an imidazole ring, a triazolering, an oxazole ring, an oxadiazole ring, a thiazole ring, athiadiazole ring, a furan ring, a thiophene ring, a selenophene ring, asilole ring, a germole ring, a phosphole ring and the like.

R₄′ to R₆′ and R₈′ are particularly preferably a hydrogen atom.

In particular, R₇′ is preferably an alkyl group, and more preferably abranched alkyl group. Specifically, the branched alkyl group may includethe following substituents (a) to (x), and is preferably substituents(a) to (h), more preferably substituents (b) to (e), and particularlypreferably substituent (c) or (d).

(X—Y) represents a bidendate ligand. The bidendate ligand represented by(X—Y) is not particularly limited, but specific examples thereofinclude, for example, substituted or unsubstituted phenylpyridine,phenylpyrazole, phenylimidazole, phenyltriazole, phenyltetrazole,pyridylpyridine, imidazolylpyridine, pyrazolylpyridine,triazolylpyridine, pyrazabole, diphenylphosphinoethylene, picolinicacid, acetylacetone and the like. Among these, phenylpyridine,phenylpyrazole, phenylimidazole, pyridylpyridine, pyrazabole, picolinicacid, acetylacetone, and the like are preferable, and phenylpyridine,picolinic acid and acetylacetone are more preferable. Acetylacetonate isparticularly preferable from the viewpoint that stability and high lightemission efficiency of the complex may be obtained. Further, thesegroups may be further substituted by the above substituent.

The preferred range of (X—Y) is the same as (X—Y) in Formula (D-1).

In the above Formula (D-2), M represents iridium, each of R₃ to R₆independently represents a hydrogen atom, an alkyl group or an arylgroup, R₃′ to R₈′ represent a hydrogen atom, an alkyl group or an arylgroup, R₃′ and R₆ may be linked by a linking group selected from—CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —O—CR₂—, —NR—CR₂— and —N═CR— toform a ring, each R independently represents a hydrogen atom, an alkylgroup, an alkenyl group, an alkynyl group, an aryl group or a heteroarylgroup, and may further have a substituent selected from a halogen atom,—R′, —OR′, —N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)₂, —CN, —NO₂,—SO₂, —SOR′, —SO₂R′ and —SO₃R′, each R′ independently represents ahydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group,an alkynyl group, an aryl group or a heteroaryl group, (X—Y) representsa ligand represented by any one of the above Formula (1-1), (1-4) or(1-15), m represents an integer of 1 to 3, n represents an integer of 0to 2, provided that m+n is preferably 3.

One of the preferable forms of the compound represented by Formula (D-1)is a compound represented by Formula (D-3).

(In Formula (D-3), M represents a metal having an atomic weight of 40 ormore. Each of R₃ to R₆ independently represents a hydrogen atom or asubstituent. Each of R₃′ to R₈′ independently represents a hydrogen atomor a substituent. R₃′ and R₆ may be linked to each other by a linkinggroup selected from —CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —O—CR₂—,—NR—CR₂— and —N═CR— to form a ring, and each R independently representsa hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, aheteroalkyl group, an aryl group or a heteroaryl group, and may furtherhave a substituent Z. Each Z independently represents a halogen atom,—R′, —OR′, —N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)₂, —CN, —NO₂,—SO₂, —SOR′, —SO₂R′ or —SO₃R′, and each R′ independently represents ahydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group,an alkynyl group, a heteroalkyl group, an aryl group or a heteroarylgroup. (X—Y) represents an ancillary ligand. m represents a value of 1to the greatest number of ligands that may be bound to the metal, and nrepresents a value of 0 to the greatest number of ligands that may bebound to the metal. m+n is the greatest number of ligands that may bebound to the metal.)

M, R₃′, (X—Y), m and n in Formula (D-3) have the same meaning as M, R₃′,(X—Y), m and n in Formula (D-1), and preferred ranges thereof are alsothe same.

Each of R₃ to R₆ independently represents a hydrogen atom or asubstituent. As the substituent represented by R₃ to R₆, thoseexemplified above for the group A of substituents may be applied.

R₃ to R₆ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied. Thesubstituent includes an alkyl group, an aryl group, a cyano group, ahalogen atom and a nitrogen-containing aromatic heterocyclic group, andmore preferably alkyl having 1 to 6 carbon atoms, an aryl group having 6to 10 carbon atoms, pyridyl, a fluorine atom and a cyano group, and evenmore preferably an alkyl group having 1 to 6 carbon atoms, a phenylgroup and a cyano group. Further, R₃ to R₆ may be linked to each otherto form a condensed ring, and a ring to be formed may include a benzenering, a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazinering, a pyridazine ring, a pyrrole ring, a pyrazole ring, an imidazolering, a triazole ring, an oxazole ring, an oxadiazole ring, a thiazolering, a thiadiazole ring, a furan ring, a thiophene ring, a selenophenering, a silole ring, a germole ring, a phosphole ring and the like.

The aryl group represented by R₃ to R₆ may include preferably asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, forexample, a phenyl group, a tolyl group, a naphthyl group and the like.

The heteroaryl group represented by R₃ to R₆ may include preferably aheteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or6-membered, substituted or unsubstituted heteroaryl group, for example,a pyridyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinazolinyl group, a cinnolinyl group, a phthalazinyl group, aquinoxalinyl group, a pyrrolyl group, an indolyl group, a furyl group, abenzofuryl group, a thienyl group, a benzothienyl group, a pyrazolylgroup, an imidazolyl group, a benzimidazolyl group, a triazolyl group,an oxazolyl group, a benzoxazolyl group, a thiazolyl group, abenzothiazolyl group, an isothiazolyl group, a benzisothiazolyl group, athiadiazolyl group, an isoxazolyl group, a benzisoxazolyl group, apyrrolidinyl group, a piperidinyl group, a piperazinyl group, animidazolidinyl group, a thiazolinyl group, a sulfolanyl group and thelike.

R₃ to R₆ include preferably a hydrogen atom, an alkyl group, a cyanogroup, a trifluoromethyl group, a perfluoroalkyl group, a dialkylaminogroup, a fluoro group, an aryl group and a heteroaryl group, morepreferably a hydrogen atom, an alkyl group, a cyano group, atrifluoromethyl group, a fluoro group and an aryl group, and even morepreferably a hydrogen atom, an alkyl group and an aryl group.

R₄ and R₆ are particularly preferably a hydrogen atom.

R₃ and R₅ are particularly preferably an alkyl group, more preferably anethyl group, an isobutyl group, a t-butyl group, a neopentyl group and amethyl group, particularly preferably an ethyl group, an isobutyl group,a neopentyl group and a methyl group, and even more preferably a methylgroup.

Each of R₄′ to R₈′ independently represents a hydrogen atom or asubstituent. As the substituent represented by R₄′ to R₈′, thoseexemplified above for the group A of substituents may be applied.

Further, R₄′ to R₈′ may further have a substituent, and as thesubstituent, those exemplified above for the group A of substituents maybe applied. In addition, R₄′ to R₈′ may be linked to each other to forma condensed ring, and a ring to be formed may include a benzene ring, apyridine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, apyridazine ring, a pyrrole ring, a pyrazole ring, an imidazole ring, atriazole ring, an oxazole ring, an oxadiazole ring, a thiazole ring, athiadiazole ring, a furan ring, a thiophene ring, a selenophene ring, asilole ring, a germole ring, a phosphole ring and the like.

The aryl group represented by R₄′ to R₃′ may include preferably asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, forexample, a phenyl group, a tolyl group, a naphthyl group and the like.

The heteroaryl group represented by R₄′ to R₈′ may include preferably aheteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or6-membered, substituted or unsubstituted heteroaryl group, for example,a pyridyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinazolinyl group, a cinnolinyl group, a phthalazinyl group, aquinoxalinyl group, a pyrrolyl group, an indolyl group, a furyl group, abenzofuryl group, a thienyl group, a benzothienyl group, a pyrazolylgroup, an imidazolyl group, a benzimidazolyl group, a triazolyl group,an oxazolyl group, a benzoxazolyl group, a thiazolyl group, abenzothiazolyl group, an isothiazolyl group, a benzisothiazolyl group, athiadiazolyl group, an isoxazolyl group, a benzisoxazolyl group, apyrrolidinyl group, a piperidinyl group, a piperazinyl group, animidazolidinyl group, a thiazolinyl group, a sulfolanyl group and thelike.

R₄′ to R₈′ include preferably a hydrogen atom, an alkyl group, a cyanogroup, a trifluoromethyl group, a perfluoroalkyl group, a dialkylaminogroup, a fluoro group, an aryl group and a heteroaryl group, morepreferably a hydrogen atom, an alkyl group, a cyano group, atrifluoromethyl group, a fluoro group and an aryl group, and even morepreferably a hydrogen atom, an alkyl group and an aryl group. Inparticular, R₄′ is preferably an alkyl group.

(X—Y) represents a bidendate ligand. The bidendate ligand represented by(X—Y) is not particularly limited, but specific examples thereofinclude, for example, substituted or unsubstituted phenylpyridine,phenylpyrazole, phenylimidazole, phenyltriazole, phenyltetrazole,pyridylpyridine, imidazolylpyridine, pyrazolylpyridine,triazolylpyridine, pyrazabole, diphenylphosphinoethylene, picolinicacid, acetylacetone and the like. Among them, phenylpyridine,phenylpyrazole, phenylimidazole, pyridylpyridine, pyrazabole, picolinicacid, acetylacetone and the like are preferable, and phenylpyridine,picolinic acid and acetylacetone are more preferable. Acetylacetonate isparticularly preferable from the viewpoint that stability and high lightemission efficiency of the complex may be obtained. Further, thesegroups may be further substituted by the above substituent.

The preferred range of (X—Y) is the same as (X—Y) in Formula (D-1).

In the above Formula (D-3), M represents iridium, each of R₃ to R₆independently represents a hydrogen atom, an alkyl group or an arylgroup, each of R₃′ to R₈′ independently represents a hydrogen atom, analkyl group or an aryl group, R₃′ and R₆ may be linked by a linkinggroup selected from —CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —NR—CR₂— and—N═CR— to form a ring, each R independently represents a hydrogen atom,an alkyl group, an alkenyl group, an alkynyl group, an aryl group or aheteroaryl group, and may further have a substituent selected from ahalogen atom, —R′, —OR′, —N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)₂,—CN, —NO₂, —SO₂, —SOR′, —SO₂R′ and —SO₃R′, each R′ independentlyrepresents a hydrogen atom, an alkyl group, a perhaloalkyl group, analkenyl group, an alkynyl group, an aryl group or a heteroaryl group,(X—Y) represents a ligand represented by any one of the above Formula(1-1), (1-4) or (1-15), m represents an integer of 1 to 3, n representsan integer of 0 to 2, provided that m+n is preferably 3.

One of the preferable forms of the compound represented by Formula (D-1)is a compound represented by Formula (D-4).

(In Formula (D-4), M represents metal having an atomic weight of 40 ormore. Each of R₃ to R₁₀ independently represents a hydrogen atom or asubstituent. Each of R₃′ to R₆′ independently represents a hydrogen atomor a substituent. R₃′ and R₁₀ may be linked to each other by a linkinggroup selected from —CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —O—CR₂—,—NR—CR₂— and —N═CR— to form a ring, and each R independently representsa hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, aheteroalkyl group, an aryl group or a heteroaryl group, and may furtherhave a substituent Z. Each Z independently represents a halogen atom,—R′, —OR′, —N(R′)₂, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)₂, —CN, —NO₂,—SO₂, —SOR′, —SO₂R′ or —SO₃R′, and each R′ independently represents ahydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group,an alkynyl group, a heteroalkyl group, an aryl group or a heteroarylgroup. (X—Y) represents an ancillary ligand. m represents a value of 1to the greatest number of ligands that may be bound to the metal, and nrepresents a value of 0 to the greatest number of ligands that may bebound to the metal. m+n is the greatest number of ligands that may bebound to the metal.)

M, R₃′, (X—Y), m and n in Formula (D-4) have the same meaning as M, R₃′,(X—Y), m and n in Formula (D-1), and preferred ranges thereof are alsothe same.

Each of R₃ to R₁₀ independently represents a hydrogen atom or asubstituent. As the substituent represented by R₃ to R₁₀, thoseexemplified above for the group A of substituents may be applied.

R₃ to R₁₀ may further have a substituent, and as the substituent, thoseexemplified above for the group A of substituents may be applied. Thesubstituent includes an alkyl group, an aryl group, a cyano group, ahalogen atom and a nitrogen-containing aromatic heterocyclic group, andmore preferably alkyl having 1 to 6 carbon atoms, an aryl group having 6to 10 carbon atoms, pyridyl, a fluorine atom and a cyano group, and evenmore preferably an alkyl group having 1 to 6 carbon atoms, a phenylgroup and a cyano group. Further, R₃ to R₁₀ may be linked to each otherto form a condensed ring, and a ring to be formed may include a benzenering, a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazinering, a pyridazine ring, a pyrrole ring, a pyrazole ring, an imidazolering, a triazole ring, an oxazole ring, an oxadiazole ring, a thiazolering, a thiadiazole ring, a furan ring, a thiophene ring, a selenophenering, a silole ring, a germole ring, a phosphole ring and the like.

The aryl group represented by R₃ to R₁₀ may include preferably asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, forexample, a phenyl group, a tolyl group, a naphthyl group and the like.

The heteroaryl group represented by R₃ to R₁₀ may include preferably aheteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or6-membered, substituted or unsubstituted heteroaryl group, for example,a pyridyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinazolinyl group, a cinnolinyl group, a phthalazinyl group, aquinoxalinyl group, a pyrrolyl group, an indolyl group, a furyl group, abenzofuryl group, a thienyl group, a benzothienyl group, a pyrazolylgroup, an imidazolyl group, a benzimidazolyl group, a triazolyl group,an oxazolyl group, a benzoxazolyl group, a thiazolyl group, abenzothiazolyl group, an isothiazolyl group, a benzisothiazolyl group, athiadiazolyl group, an isoxazolyl group, a benzisoxazolyl group, apyrrolidinyl group, a piperidinyl group, a piperazinyl group, animidazolidinyl group, a thiazolinyl group, a sulfolanyl group and thelike.

R₃ to R₁₀ include preferably a hydrogen atom, an alkyl group, a cyanogroup, a trifluoromethyl group, a perfluoroalkyl group, a dialkylaminogroup, a fluoro group, an aryl group and a heteroaryl group, morepreferably a hydrogen atom, an alkyl group, a cyano group, atrifluoromethyl group, a fluoro group and an aryl group, and even morepreferably a hydrogen atom, an alkyl group, a cyano group and an arylgroup, and particularly preferably a hydrogen atom, an alkyl group andan aryl group.

R₃ to R₆ and R₃ to R₁₀ are particularly preferably a hydrogen atom.

R₇ is particularly preferably an alkyl group, preferably a methyl group,an isobutyl group and a neopentyl group, and more preferably a methylgroup.

Each of R₃′ to R₆′ independently represents a hydrogen atom or asubstituent. As the substituent represented by R₃′ to R₆′, thoseexemplified above for the group A of substituents may be applied.

Further, R₃′ to R₆′ may further have a substituent, and as thesubstituent, those exemplified above for the group A of substituents maybe applied. In addition, R₃′ to R₆′ may be linked to each other to forma condensed ring, and a ring to be formed may include a benzene ring, apyridine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, apyridazine ring, a pyrrole ring, a pyrazole ring, an imidazole ring, atriazole ring, an oxazole ring, an oxadiazole ring, a thiazole ring, athiadiazole ring, a furan ring, a thiophene ring, a selenophene ring, asilole ring, a germole ring, a phosphole ring and the like.

The aryl group represented by R₃′ to R₆′ may include preferably asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, forexample, a phenyl group, a tolyl group, a naphthyl group and the like.

The heteroaryl group represented by R₃′ to R₆′ may include preferably aheteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or6-membered, substituted or unsubstituted heteroaryl group, for example,a pyridyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinazolinyl group, a cinnolinyl group, a phthalazinyl group, aquinoxalinyl group, a pyrrolyl group, an indolyl group, a furyl group, abenzofuryl group, a thienyl group, a benzothienyl group, a pyrazolylgroup, an imidazolyl group, a benzimidazolyl group, a triazolyl group,an oxazolyl group, a benzoxazolyl group, a thiazolyl group, abenzothiazolyl group, an isothiazolyl group, a benzisothiazolyl group, athiadiazolyl group, an isoxazolyl group, a benzisoxazolyl group, apyrrolidinyl group, a piperidinyl group, a piperazinyl group, animidazolidinyl group, a thiazolinyl group, a sulfolanyl group and thelike.

R₃′ to R₆′ include preferably a hydrogen atom, an alkyl group, a cyanogroup, a trifluoromethyl group, a perfluoroalkyl group, a dialkylaminogroup, a fluoro group, an aryl group and a heteroaryl group, morepreferably a hydrogen atom, an alkyl group, a cyano group, atrifluoromethyl group, a fluoro group and an aryl group, and even morepreferably a hydrogen atom, an alkyl group and an aryl group.

(X—Y) represents a bidendate ligand. The bidendate ligand represented by(X—Y) is not particularly limited, but specific examples thereofinclude, for example, substituted or unsubstituted phenylpyridine,phenylpyrazole, phenylimidazole, phenyltriazole, phenyltetrazole,pyridylpyridine, imidazolylpyridine, pyrazolylpyridine,triazolylpyridine, pyrazabole, diphenylphosphinoethylene, picolinicacid, acetylacetone and the like. Among them, phenylpyridine,phenylpyrazole, phenylimidazole, pyridylpyridine, pyrazabole, picolinicacid, acetylacetone and the like are preferable, and phenylpyridine,picolinic acid and acetylacetone are more preferable, and penylpyridineis particularly preferable from the viewpoint of stability of thecomplex. Further, these groups may be further substituted by the abovesubstituent.

The preferred range of (X—Y) is the same as (X—Y) in Formula (D-1).

In the above Formula (D-4), M represents iridium, each of R₃ to R₁₀independently represents a hydrogen atom, an alkyl group or an arylgroup, each of R₃′ to R₆′ independently represents a hydrogen atom, analkyl group or an aryl group, R₃′ and R₁₀ may be linked by a linkinggroup selected from —CR₂—CR₂—, —CR═CR—, —CR₂—, —O—, —NR—, —O—CR₂—,—NR—CR₂— and —N═CR— to form a ring, each R independently represents ahydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, anaryl group or a heteroaryl group, and may further have a substituentselected from a halogen atom, —R′, —OR′, —N(R′)₂, —SR′, —C(O)R′,—C(O)OR′, —C(O)N(R′)₂, —CN, —NO₂, —SO₂, —SOR′, —SO₂R′ and —SO₃R′, eachR′ independently represents a hydrogen atom, an alkyl group, aperhaloalkyl group, an alkenyl group, an alkynyl group, an aryl group ora heteroaryl group, (X—Y) represents a ligand represented by any one ofthe above Formula (1-1), (1-4) or (1-15), m represents an integer of 1to 3, n represents an integer of 0 to 2, but m+n is preferably 3.

The compounds represented by Formulas (D-1) to (D-4) may be synthesizedwith reference to, for example, various known synthetic methods such asInorg. Chem., 30, 1685-1687 (1991), J. Am. Chem. Soc., vol. 123, 4304(2001), Inorg. Chem., vol. 40, 1704-1711(2001), Inorg. Chem., 41,3055-3066 (2002), Eur. J. Org. Chem., 4, 695-709 (2004) and the like,and International Publication No. WO09/073,245 and InternationalPublication No. WO08/109,824.

Preferred specific examples of the compounds represented by Formulas(D-1) to (D-4) are represented below, but are not limited thereto.

Further, in the structural formulas, acac represents a ligand(acetylacetonate) having the following structure.

In the present invention, the compound represented by Formula (D-1) isincluded in a light emitting layer from the viewpoint of improving lightemission efficiency and durability (in particular, durability whendriving at a high temperature), but the use thereof is not limited, andmay be included in any layer in addition to the light emitting layerwithin the organic layer. It is preferred that as a layer whichintroduces the compound represented by Formula (D-1), the compound isincluded in any one of a hole injection layer, a hole transportinglayer, an electron transporting layer, an electron injection layer, anexciton blocking layer and a charge blocking layer, or a pluralitythereof in addition to a light emitting layer.

[A Composition Containing a Compound Represented by Formula (1) and aCompound Represented by Formula (D-1)]

The present invention also relates to a composition containing thecompound represented by Formula (1) and the compound represented byFormula (D-1).

The content of the compound represented by Formula (1) included in thecomposition of the present invention is preferably 50 to 99% by mass,and more preferably 70 to 95% by mass.

The content of the compound represented by Formula (D-1) included in thecomposition of the present invention is preferably 1 to 30% by mass, andmore preferably 5 to 15% by mass.

Other components which may be contained in the composition of thepresent invention may be organic materials or inorganic materials, andas organic materials, materials which are exemplified as a hostmaterial, a fluorescent light emitting material, and a phosphorescentlight emitting material, which are described below, may be applied.

The composition of the present invention may form an organic layer of anorganic electroluminescence device by dry film-forming methods such as avapor deposition method, a sputtering method, and the like, a transfermethod, a printing method and the like.

[Organic Electroluminescence Device]

An organic electroluminescence device of the present invention is anorganic electroluminescence device, including, on a substrate, a pair ofelectrodes and at least one layer of an organic layer including a lightemitting layer containing a light emitting material between theelectrodes, wherein the light emitting layer contains at least each oneof the compound represented by Formula (1) and the compound representedby Formula (D-1).

In the organic electroluminescence device of the present invention, thelight emitting layer is an organic layer, but may further have aplurality of organic layers.

Due to properties of the luminescence device, at least one electrode ofthe anode and cathode is preferably transparent or semi-transparent.

FIG. 1 illustrates an example of the configuration of an organicelectroluminescence device according to the present invention. Theorganic electroluminescence device 10 according to the presentinvention, which is illustrated in FIG. 1, is on a supporting substrate2, and a light emitting layer 6 is interposed between an anode 3 and acathode 9. Specifically, a hole injection layer 4, a hole transportinglayer 5, the light emitting layer 6, a hole blocking layer 7, and anelectron transporting layer 8 are stacked in this order between theanode 3 and the cathode 9.

<Configuration of an Organic Layer>

The layer configuration of the organic layer is not particularlylimited, and may be appropriately selected according to the use andpurpose of the organic electroluminescence device, but is preferablyformed on the transparent electrode or on the rear electrode. In thiscase, the organic layer is formed on the front surface or one surface onthe transparent electrode or the rear electrode.

The shape, size, thickness and the like of the organic layer are notparticularly limited and may be appropriately selected according to thepurpose.

The specific layer configuration may include the followings, but thepresent invention is not limited to the configurations.

Anode/hole transporting layer/light emitting layer/electron transportinglayer/cathode,

Anode/hole transporting layer/light emitting layer/blockinglayer/electron transporting layer/cathode,

Anode/hole transporting layer/light emitting layer/blockinglayer/electron transporting layer/electron injection layer/cathode,

Anode/hole injection layer/hole transporting layer/light emittinglayer/blocking layer/electron transporting layer/cathode, and

Anode/hole injection layer/hole transporting layer/light emittinglayer/blocking layer/electron transporting layer/electron injectionlayer/cathode.

The device configuration, substrate, cathode, and anode of the organicelectroluminescence device are described in detail in, for example,Japanese Patent Application Laid-Open No. 2008-270736, and the subjectmatters described in the publication may be applied to the presentinvention.

<Substrate>

It is preferred that the substrate which is used in the presentinvention is a substrate which does not scatter or decay light generatedfrom the organic layer. In the case of an organic material, it ispreferred that the organic material is excellent in heat resistance,dimensional stability, solvent resistance, electrical insulationproperties and processibility.

<Anode>

Typically, the anode may have a function as an electrode for supplyingholes into the organic layer, is not particularly limited with respectto shape, structure, size, and the like and may be appropriatelyselected among the known electrode materials depending upon a use orpurpose of the luminescence device. As described above, the anode isusually provided as a transparent anode.

<Cathode>

Typically, the cathode may have a function as an electrode for injectingelectrons into the organic layer, is not particularly limited withrespect to shape, structure, size and the like, and may be appropriatelyselected among the known electrode materials depending upon a use orpurpose of the luminescence device.

With respect to the substrate, the anode, and the cathode, subjectmatters described in paragraph Nos. [0070] to [0089] of Japanese PatentApplication Laid-Open No. 2008-270736 may be applied to the presentinvention.

<Organic Layer>

An organic layer in the present invention will be described.

—Formation of an Organic Layer—

In the organic electroluminescence device of the present invention, eachorganic layer may be appropriately formed by any one of dry film-formingmethods such as a vapor deposition method, a sputtering method, and thelike, and wet film-forming methods (wet process) such as a transfermethod, a printing method, a spin-coat method, and the like.

In the present invention, it is preferred that a light emitting layercontaining at least each one of the compound represented by Formula (1)and the compound represented by Formula (D-1) is formed by the wetprocess from the viewpoint of reducing manufacturing costs.

(Light Emitting Layer)

The light emitting layer of the present invention contains at least eachone of the compound represented by Formula (1) and the compoundrepresented by Formula (D-1).

<Light Emitting Material>

A light emitting material in the present invention is preferably thecompound represented by Formula (D-1).

The light emitting material in the light emitting layer is preferablyincluded in an amount of 0.1% by mass to 50% by mass, more preferably 1%by mass to 50% by mass from the viewpoint of durability and externalquantum efficiency, and even more preferably 2% by mass to 40% by mass,with respect to the mass of the total compound which generally forms thelight emitting layer in the light emitting layer.

The compound represented by Formula (D-1) in the light emitting layer ispreferably included in an amount of 1% by mass to 30% by mass, and morepreferably 4% by mass to 20% by mass from, the viewpoint of durabilityand external quantum efficiency in the light emitting layer.

A thickness of the light emitting layer is not particularly limited, buttypically, the thickness is preferably 2 nm to 500 nm. Among the numbersof thicknesses, from the viewpoint of external quantum efficiency, thethickness of the light emitting layer is more preferably 3 nm to 200 nm,and even more preferably 5 nm to 100 nm.

The light emitting layer in the device of the present invention may havea configuration of a mixed layer of a light emitting material and a hostmaterial.

The light emitting layer may be a fluorescent light emitting material ora phosphorescent light emitting material, and the dopant may be usedeither alone or in combination of two or more kinds. The host materialis preferably a charge transporting material. The host material may beused either alone or in combination of two or more kinds, and may have,for example, a configuration of a mixture of an electron transportinghost material and a hole transporting host material. Further, the hostmaterial may include a material which does not have a chargetransporting property in the light emitting layer and does not emitlight.

In addition, the light emitting layer may be a single layer or a multilayer of two or more layers. Furthermore, each light emitting layer mayemit light with different light emission colors.

The present invention also relates to a light emitting layer includingthe compound represented by Formula (1) and the compound represented byFormula (D-1). The light emitting layer of the present invention may beused in an organic electroluminescence device.

<Host Material>

The host material used in the present invention may include thefollowing compounds. Examples of the host material include pyrrole,indole, carbazole (for example, CBP (4,4′-di(9-carbazoyl)biphenyl)),azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole,imidazole, thiophene, polyarylalkane, pyrazoline, pyrazolone,phenylenediamine, arylamine, amino substituted chalcone,styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatictertiary amine compounds, styrylamine compounds, porphyrin-basedcompounds, polysilane-based compounds, poly(N-vinylcarbazole),aniline-based copolymers, electrically conductive high-molecularoligomers such as thiophene oligomers, polythiophene and the like,organosilanes, carbon films, pyridine, pyrimidine, triazine, imidazole,pyrazole, triazole, oxazole, oxadiazole, fluorenone,anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide,carbodiimide, fluorenylidenemethane, distyrylpyrazine,fluorine-substituted aromatic compounds, heterocyclic tetracarboxylicanhydrides such as naphthalene perylene and the like, phthalocyanine, avariety of metal complexes represented by metal complexes of a8-quinolinol derivative, metal phthalocyanine, and metal complexeshaving benzoxazole or benzothiazole as the ligand thereof, andderivatives thereof (which may have a substituent or a condensed ring),and the like.

In the light emitting layer in the present invention, it is preferredthat the lowest triplet excitation energy (T₁ energy) of the hostmaterial is higher than the T₁ energy of the phosphorescent lightemitting material from the viewpoint of color purity, light emissionefficiency and driving durability.

The host material is preferably the compound represented by Formula (1).

Further, although the content of the host compound included in thepresent invention is not particularly limited, the content is preferably15% by mass to 95% by mass with respect to the total mass of thecompounds forming the light emitting layer, from the viewpoint of lightemission efficiency and driving voltage.

The compound represented by Formula (1) in the light emitting layer ispreferably 15% by mass to 95% by mass, and more preferably 40% by massto 96% by mass with respect to the total mass of the compounds formingthe light emitting layer, from the viewpoint of light emissionefficiency and driving voltage in the light emitting layer.

(Fluorescent Light Emitting Material)

Examples of the fluorescent light emitting material which may be used inthe present invention include, for example, benzoxazole derivatives,benzoimidazole derivatives, benzothiazole derivatives, styrylbenzenederivatives, polyphenyl derivatives, diphenylbutadiene derivatives,tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarinderivatives, condensed aromatic compounds, perynone derivatives,oxadiazole derivatives, oxazine derivatives, aldazine derivatives,pyralidine derivatives, cyclopentadiene derivatives, bisstyrylanthracenederivatives, quinacridone derivatives, pyrrolopyridine derivatives,thiadiazolopyridine derivatives, cyclopentadiene derivatives,styrylamine derivatives, diketopyrrolopyrole derivatives, aromaticdimethylidine compounds, various complexes represented by a complex of8-quinolinol derivatives or a complex of pyromethene derivatives and thelike, polymer compounds such as polythiophene, polyphenylene,polyphenylenevinylene, and the like, compounds such as organic silanederivatives, and the like.

(Phosphorescent Light Emitting Material)

Examples of the phosphorescent light emitting material which may be usedin the present invention include phosphorescent light emitting compoundsand the like as described in patent documents such as U.S. Pat. No.6,303,238B1, U.S. Pat. No. 6,097,147, WO00/57676, WO00/70655,WO01/08230, W001/39234A2, W001/41512A1, WO02/02714A2, WO02/15645A1,WO02/44189A1, WO05/19373A2, Japanese Patent Application Laid-Open No.2001-247859, Japanese Patent Application Laid-Open No. 2002-302671,Japanese Patent Application Laid-Open No. 2002-117978, Japanese PatentApplication Laid-Open No. 2003-133074, Japanese Patent ApplicationLaid-Open No. 2002-235076, Japanese Patent Application Laid-Open No.2003-123982, Japanese Patent Application Laid-Open No. 2002-170684,EP1211257, Japanese Patent Application Laid-Open No. 2002-226495,Japanese Patent Application Laid-Open No. 2002-234894, Japanese PatentApplication Laid-Open No. 2001-247859, Japanese Patent ApplicationLaid-Open No. 2001-298470, Japanese Patent Application Laid-Open No.2002-173674, Japanese Patent Application Laid-Open No. 2002-203678,Japanese Patent Application Laid-Open No. 2002-203679, Japanese PatentApplication Laid-Open No. 2004-357791, Japanese Patent ApplicationLaid-Open No. 2006-256999, Japanese Patent Application Laid-Open No.2007-19462, Japanese Patent Application Laid-Open No. 2007-84635,Japanese Patent Application Laid-Open No. 2007-96259, and the like.Among them, as for light emitting material (light emitting dopant), anIr complex, a Pt complex, a Cu complex, a Re complex, a W complex, a Rhcomplex, a Ru complex, a Pd complex, an Os complex, an Eu complex, a Tbcomplex, a Gd complex, a Dy complex and a Ce complex are even morepreferable. An Ir complex, a Pt complex or a Re complex are particularlypreferable, and among them, an Ir complex, a Pt complex or a Re complexincluding at least one coordination mode of a metal-carbon bond, ametal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond arepreferable. Further, from the viewpoint of light emission efficiency,driving durability, chromaticity and the like, an Ir complex, a Ptcomplex or a Re complex including a tridentate or higher polydentateligand are particularly preferable.

The content of the phosphorescent light emitting material included inthe light emitting layer is preferably 0.1% by mass to 50% by mass, morepreferably 0.2% by mass to 50% by mass, even more preferably 0.3% bymass to 40% by mass, and most preferably 4% by mass to 30% by mass, withrespect to the total mass of the light emitting layer.

The content of the phosphorescent light emitting material which may beused in the present invention is preferably 0.1% by mass to 50% by mass,more preferably 1% by mass to 40% by mass, and most preferably 4% bymass to 30% by mass, with respect to the total mass of the lightemitting layer. In particular, within the range of 4% by mass to 30% bymass, the luminescence chromaticity of the organic electroluminescencedevice has low dependency on the concentration of the phosphorescentlight emitting material added.

—Electron Injection Layer and Electron Transporting Layer—

Each of the hole injection layer and the hole transporting layer is alayer having a function of accepting a hole from the anode or the anodeside to transport the hole into the cathode side.

For the present invention, a hole injection layer or hole transportinglayer containing an electron accepting dopant is preferably included asan organic layer.

—Electron Injection Layer and Electron Transporting Layer—

Each of the electron injection layer and the electron transporting layeris a layer having a function of accepting an electron from the cathodeor the cathode side to transport the electron into the anode side.

With respect to the hole injection layer, the hole transporting layer,the electron injection layer and the electron transporting layer, thesubject matters described in paragraph Nos. [0165] to [0167] of JapanesePatent Application Laid-Open No. 2008-270736 may be applied to thepresent invention.

—Hole Blocking Layer—

The hole blocking layer is a layer having a function of preventing ahole transported to the light emitting layer from the anode side frompenetrating to the cathode side. In the present invention, the holeblocking layer may be provided as an organic layer adjacent to the lightemitting layer on the cathode side.

Examples of the organic compound constituting the hole blocking layerinclude an aluminum complex such asaluminum(III)bis(2-methyl-8-quinolinato)-4-phenylphenolate (simplyreferred to as BAlq) and the like, triazole derivatives, andphenanthroline derivatives such as2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (simply referred to asBCP) and the like.

The thickness of the hole blocking layer is preferably 1 nm to 500 nm,more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100nm.

The hole blocking layer may have a single layer structure composed ofone or two or more kinds of the above-described materials or may have amultilayer structure composed of a plurality of layers of the same ordifferent compositions.

—Electron Blocking Layer—

The electron blocking layer is a layer having a function of preventingan electron transported to the light emitting layer from the cathodeside from penetrating to the anode side. In the present invention, theelectron blocking layer may be provided as an organic layer adjacent tothe light emitting layer on the anode side.

Examples of the organic compound constituting the electron blockinglayer include those described above as the hole transporting material.

The thickness of the electron blocking layer is preferably 1 nm to 500nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to100 nm.

The electron blocking layer may have a single layer structure composedof one or two or more kinds of the above-described materials or may havea multilayer structure composed of a plurality of layers of the same ordifferent compositions.

<Protective Layer>

In the present invention, the entire organic EL device may be protectedby a protective layer.

With respect to the protective layer, the subject matters described inparagraph Nos. and [0170] of Japanese Patent Application Laid-Open No.2008-270736, may be applied to the present invention.

<Sealing Vessel>

In the device of the present invention, the entire device may be sealedusing a sealing vessel.

With respect to the sealing vessel, the subject matters described inparagraph No. of Japanese Patent Application Laid-Open No. 2008-270736may be applied to the present invention.

(Driving)

In the organic electroluminescence device of the present invention,light emission may be obtained by applying a voltage (typically 2 voltsto 15 volts) of direct current (may include an alternating currentcomponent if necessary) or a current of direct current between the anodeand the cathode.

With respect to the driving method of the organic electroluminescencedevice of the present invention, driving methods described in eachofficial gazette of Japanese Patent Application Laid-Open No. Hei2-148687, Japanese Patent Application Laid-Open No. Hei 6-301355,Japanese Patent Application Laid-Open No. Hei 5-29080, Japanese PatentApplication Laid-Open No. Hei 7-134558, Japanese Patent ApplicationLaid-Open No. Hei 8-234685, and Japanese Patent Application Laid-OpenNo. Hei 8-241047, and Japanese Patent No. 2784615, U.S. Pat. Nos.5,828,429, and 6,023,308, and the like may be applied.

The light collection efficiency of the luminescence device of thepresent invention may be enhanced by various known devices. For example,the light collection efficiency may be enhanced to enhance the externalquantum efficiency by processing the substrate surface shape (forexample, forming a fine uneven pattern), by controlling the refractiveindex of the substrate ITO layer or organic layer, by controlling thefilm thickness of the substrate-ITO layer-organic layer, and the like.

The luminescence device of the present invention may be in a so-calledtop emission mode of collecting light emission from the anode side.

The organic EL device in the present invention may have a resonatorstructure. For example, a multilayer mirror composed of a plurality oflaminated films having the different refractive index, a transparent orsemi-transparent electrode, a light emitting layer, and a metalelectrode are superimposed on a transparent substrate. Light generatedin the light emitting layer is repeatedly reflected and resonatedbetween the multilayer film mirror and the metal electrode as areflection plate.

In another preferred aspect, each of a transparent or semi-transparentelectrode and a metal electrode functions as a reflecting plate on atransparent substrate, and light generated in the light emitting layerrepeats reflection and resonates therebetween.

In order to form a resonance structure, the effective refractive indexof two reflecting plates and the optical path length determined from therefractive index and thickness of each layer between the reflectingplates may be adjusted to be optimal values to obtain a desiredresonance wavelength. The calculating formula in the case of the firstaspect is described in Japanese Patent Application Laid-Open No. Hei9-180883. The calculating formula in the case of the second aspect isdescribed in Japanese Patent Application Laid-Open No. 2004-127795.

The external quantum efficiency of the organic electroluminescencedevice of the present invention is preferably 5% or more, and morepreferably 7% or more. As values of external quantum efficiency, amaximum value of external quantum efficiency, or a value of externalquantum efficiency near 100 to 300 cd/m² may be used when driving thedevice at 20° C.

The internal quantum efficiency of the organic electroluminescencedevice of the present invention is preferably 30% or more, morepreferably 50% or more, and even more preferably 70% or more. Theinternal quantum efficiency of the device is calculated by dividing theexternal quantum efficiency by the light collection efficiency. Althoughtypical organic EL devices have an light collection efficiency of about20%, it is possible to achieve a light collection efficiency of 20% ormore by studying the shape of the substrate, the shape of the electrode,the film thickness of the organic layer, the film thickness of theinorganic layer, the refractive index of the organic layer, therefractive index of the inorganic layer and the like.

The organic electroluminescence device of the present invention hasultra-high power emission wavelength (maximum strength wavelength of theemission spectrum) of preferably 350 nm or more and 700 nm or less, morepreferably 350 nm or more and 600 nm or less, even more preferably 400nm or more and 520 nm or less, and particularly preferably 400 nm ormore and 465 nm or less.

(Use of Luminescence Device of the Present Invention)

The luminescence device of the present invention may be suitably usedfor light emission apparatuses, pixels, display devices, displays,backlights, electrophotography, illumination light sources, recordinglight sources, exposure light sources, reading light sources,indicators, signboards, interiors, optical communication or the like. Inparticular, the luminescence device of the present invention ispreferably used for a device that is driven in a region with highluminescence luminance intensity, such as a light emission apparatus, anillumination apparatus, a display apparatus, and the like.

Next, the light emission apparatus of the present invention will bedescribed by referring to FIG. 2.

The light emission apparatus of the present invention is configured byusing the above-described organic electroluminescence device.

FIG. 2 is a cross-sectional view schematically illustrating an exampleof a light emission apparatus of the present invention:

The light emission apparatus 20 of FIG. 2 is composed of a transparentsubstrate (supporting substrate) 2, an organic electroluminescencedevice 10, a sealing vessel 16, and the like.

The organic electroluminescence device 10 is configured by sequentiallylaminating an anode (first electrode) 3, an organic layer 11, and acathode (second electrode) 9 on the substrate 2. Further, a protectivelayer 12 is laminated on the cathode 9, and the sealing vessel 16 isfurther provided on the protective layer 12 through an adhesive layer14. In addition, a part of each of electrodes 3 and 9, a partition wall,an insulating layer, and the like are omitted.

Here, as the adhesive layer 14, a photocurable or thermosetting adhesivesuch as an epoxy resin, and the like may be used and, for example, athermosetting adhesive sheet may also be used.

The use of the light emission apparatus of the present invention is notparticularly limited and, for example, the light emission apparatus maybe used not only for an illumination apparatus but also as a displayapparatus such as a television set, a personal computer, a cellularphone, an electronic paper and the like.

(Illumination Apparatus)

Next, an illumination apparatus according to an embodiment of thepresent invention will be described by referring to FIG. 3.

FIG. 3 is a cross-sectional view schematically illustrating an exampleof the illumination apparatus according to the embodiment of the presentinvention.

The illumination apparatus 40 according to the embodiment of the presentinvention includes, as illustrated in FIG. 3, the above-describedorganic EL device 10 and a light scattering member 30. Morespecifically, the illumination apparatus 40 is configured such that thesubstrate 2 of the organic EL device 10 and the light scattering member30 are in contact with each other.

The light scattering member 30 is not particularly limited so long asthe member may scatter light, but in FIG. 3, a member obtained bydispersing microparticulates 32 in a transparent substrate 31 is used.Suitable examples of the transparent substrate 31 include a glasssubstrate. Suitable examples of the microparticulate 32 include atransparent resin microparticulate. As the glass substrate and thetransparent resin microparticulate, products known in the art may beused. In such an illumination apparatus 40, when light emitted from theorganic electroluminescence device 10 is incident on a light incidentsurface 30A of the scattering member 30, the incident light is scatteredby the light scattering member 30 and the scattered light is reflectedas illuminating light from a light reflecting surface 30B.

EXAMPLE

(Synthesis of Exemplary Compound 156 (C-6)

Exemplary compound (156) of a compound represented by Formula (1) may beprepared by the following reaction scheme.

2 equivalents of phenylhydrazine hydrochloride were added to1,2-cyclohexanedione in ethanol, and 0.1 equivalents of concentratedsulfuric acid was added dropwise under nitrogen atmosphere over 5 min.Thereafter, the solution was refluxed at a boiling temperature for 4 hr,and intermediate 1 was obtained in a yield of 90%. Intermediate 1 wasstirred in a mixed solvent of acetic acid-trifluoroacetic acid at 100°C. for 15 hr, and intermediate 2 was obtained in a yield of 39%.Intermediate 2, 0.05 equivalents of palladium acetate, 0.15 equivalentsof tri(t-butyl)phosphine, 2.4 equivalents of sodium-tert-butoxide, and 1equivalent of iodobenzene were dissolved in xylene and refluxed at aboiling temperature for 10 hr to synthesize intermediate 3 (yield: 35%).Intermediate 3, 0.05 equivalents of palladium acetate, 0.15 equivalentsof tri(t-butyl)phosphine, 2.4 equivalents of rubidium carbonate and 0.5equivalent of intermediate 4 were dissolved in xylene and refluxed at aboiling temperature to react for 13 hr. Ethyl acetate and water wereadded to the reaction mixture to separate an organic phase, the organicphase was washed with water and saturated saline solution andconcentrated under reduced pressure, and the obtained residue waspurified by silica gel column chromatography, recrystallization,sublimation purification, and the like to obtain exemplary compound 156in a yield of 56%. Further, the compound C-6 used in Example correspondsto exemplary compound 156.

(Synthesis of Exemplary Compound 162 (C-4))

Exemplary compound (162) of a compound represented by Formula (1) may beprepared by the following reaction scheme.

3,3′-dibromophenyl and 0.05 equivalents of palladium acetate, 0.15equivalents of tri(t-butyl)phosphine, 2.4 equivalents of rubidiumcarbonate and 2 equivalents of 3 were dissolved in xylene and refluxedat a boiling temperature to react for 13 hr. Ethyl acetate and waterwere added to the reaction mixture to separate an organic phase, theorganic phase was washed with water and saturated saline solution andconcentrated under reduced pressure, and the obtained residue waspurified by silica gel column chromatography, recrystallization,sublimation purification and the like to obtain exemplary compound 162in a yield of 76%. Further, the compound C-4 used in Example correspondsto exemplary compound 162.

(Synthesis of Exemplary Compound 138 (C-1))

Exemplary compound 138 (C-1) of a compound represented by Formula (1)may be prepared by the following reaction scheme.

2 equivalents of phenylhydrazine hydrochloride were added to1,2-cyclohexanedione in ethanol, and 0.1 equivalents of concentratedsulfuric acid was added dropwise under nitrogen atmosphere over 5 min.Thereafter, the solution was refluxed at a boiling temperature for 4 hr,and intermediate 4 was obtained in a yield of 90%. Intermediate 4 wasstirred under a mixed solvent of acetic acid-trifluoroacetic acid at100° C. for 15 hr, and intermediate 5 was obtained in a yield of 39%.Intermediate 5, 0.05 equivalents of palladium acetate, 0.15 equivalentsof tri(t-butyl)phosphine, 2.4 equivalents of sodium-tert-butoxide and2.2 equivalents of iodobenzene were dissolved in xylene and refluxed ata boiling temperature to react for 10 hr. Ethyl acetate and water wereadded to the reaction mixture to separate an organic phase, the organicphase was washed with water and saturated saline solution and thenconcentrated under reduced pressure, and the obtained residue waspurified by silica gel column chromatography, recrystallization,sublimation purification and the like to obtain exemplary compound 138in a yield of 66%. Further, compound C-1 used in the Example correspondsto exemplary compound 138.

(Synthesis of Exemplary Compound 196 (C-14))

Exemplary compound 196 (C-14) of a compound represented by Formula (1)may be prepared by the following reaction scheme.

1 equivalent of cyanil chloride was dissolved in dry THF. 32%phenylmagnesium bromide THF solution (2.5 equivalents) was addeddropwise in an ice bath under nitrogen atmosphere and stirred for 2 hrto synthesize intermediate 6 (yield: 37%). Intermediate 2, 0.05equivalents of palladium acetate, 0.15 equivalents oftri(t-butyl)phosphine, 2.4 equivalents of sodium-tert-butoxide and 1equivalent of iodobenzene were dissolvdd in xylene and refluxed at aboiling temperature for 10 hr to synthesize intermediate 7 (yield: 35%).1.1 equivalents of sodium hydride was dispersed in dryN,N′-dimethylformamide (DMF) and stirred under nitrogen atmosphere. ADMF solution of 1 equivalent of intermediate 7 was added dropwise andstirred for 1 hr. Thereafter, a DMF solution of 1 equivalent ofintermediate 6 was added dropwise and stirred for 3 hr. Water was added,and precipitated crystals were separated by filtration.Recrystallization was performed from an ethanol/chloroform solution andthe resulting solution was subjected to purification by sublimation toobtain exemplary compound 196 in a yield of 32%. Further, compound C-14used in the Example corresponds to exemplary compound 196.

Example 1 Manufacture of Organic Electroluminescence Device ComparativeExample 1-1

A washed ITO substrate was put in a vapor deposition apparatus tovapor-deposit copper phthalocyanine to a thickness of 10 nm, and NPD(N,N′-di-a-naphthyl-N,N′-diphenyl)benzidine) was vapor-deposited thereonto a thickness of 40 nm (hole transporting layer). Thereon, A-1 and C-1were vapor-deposited at a ratio of 9:91 (mass ratio) to a thickness of30 nm (light emitting layer), and H-1 was vapor-deposited thereon to athickness of 5 nm (adjacent layer). Thereon, BAlq[bis-(2-methyl-8-quinolinolate)-4-(phenylphenolate)aluminum] wasvapor-deposited to a thickness of 30 nm (electron transporting layer).Thereon, lithium fluoride was vapor-deposited to a thickness of about 3nm, and aluminum was vapor-deposited thereon to a thickness of 60 nm.This was placed in a glove box substituted with argon gas so as not tobe exposed to the atmosphere and sealed using a stainless steel-madesealing tube and a UV-curable adhesive (XNR5516HV, manufactured byNagase-CHIBA Ltd.) to obtain an organic electroluminescence device inComparative Example 1-1. A direct current constant voltage was appliedto the EL device to emit light by means of a source measure unit Model2400 manufactured by Toyo Technica, and, as a result, a phosphorescentlight emission derived from A-1 could be obtained.

Examples 1-1 to 1-198 and Comparative Examples 1-2 to 1-16

A device was manufactured and evaluated in the same manner as inComparative Example 1-1, except that the compounds used for the lightemitting material and the host material were changed into thosedescribed in Table 1. In any of the devices, a phosphorescent lightemission derived from a light emitting material used could be obtained.The obtained results were incorporated into Table 1.

(Measurement of Driving Voltage)

Each organic electroluminescence device was set on an emission spectrummeasurement system (ELS 1500), manufactured by Shimadzu Corporation, andan applied voltage at the time when the luminance intensity was 100cd/m² was measured.

(Evaluation of External Quantum Efficiency)

Light emission was performed by applying a direct current constantvoltage to each organic electroluminescence device using a sourcemeasure unit MODEL 2400, manufactured by Toyo Technica. An externalquantum efficiency (%) was calculated from the front luminance intensityat the time of 1000 cd/m2.

(Evaluation of Driving Durability)

Each organic electroluminescence device was set on an OLED test system,MODEL ST-D, manufactured by Tokyo Systems Development Co., Ltd. anddriven in a constant current mode under a condition of an initialluminance intensity of 1,000 cd/cm² at an ambient air temperature of 70°C., thereby measuring a half-luminance intensity time.

Further, each of values of the devices in Comparative Example 1-1,Comparative Example 2-1, Comparative Example 3-1, and ComparativeExample 4-1 was made to be 100, and with reference to those values,relative values are shown in Tables 1 to 4.

TABLE 1 Half- luminance intensity time (relative value) at an Externalambient air Light emitting layer Driving quantum temperature of Lightemitting Host voltage (V) at efficiency (%) 70° C. and material material1000 cd/m² at 1000 cd/m² 1000 cd/m² Comparative A-1 C-1 10.6 6.2 100example 1-1 Comparative A-1 C-3 11.1 5.9 104 example 1-2 Comparative A-1C-6 10.8 6 97 example 1-3 Comparative A-1 C-8 11.8 5.7 85 example 1-4Comparative A-1 C-9 11.1 5.9 103 example 1-5 Comparative A-1 H-1 10.885.8 95 example 1-6 Comparative A-2 H-1 10.3 7.6 151 example 1-7Comparative A-3 H-1 10.2 7.5 68 example 1-8 Comparative A-5 H-1 10.1 7.8201 example 1-9 Comparative A-7 H-1 10.6 6.5 85 example 1-10 Example 1-1A-2 C-1 9.7 8.2 204 Example 1-2 A-2 C-3 9.6 8.3 233 Example 1-3 A-2 C-49.5 8.7 244 Example 1-4 A-2 C-5 9.3 8.7 198 Example 1-5 A-2 C-6 9.7 8.4253 Example 1-6 A-2 C-7 9.7 8.2 262 Example 1-7 A-3 C-1 9.8 8.7 133Example 1-8 A-3 C-2 9.9 8.8 142 Example 1-9 A-3 C-4 9.8 8.9 157 Example1-10 A-3 C-5 9.5 9.4 133 Example 1-11 A-3 C-6 9.6 8.8 159 Example 1-12A-3 C-8 9.9 8.6 138 Example 1-13 A-3 C-9 9.8 8.8 148 Example 1-14 A-4C-2 9.8 9.1 249 Example 1-15 A-4 C-3 9.9 9.2 257 Example 1-16 A-4 C-49.7 9 296 Example 1-17 A-4 C-5 9.2 9.6 221 Example 1-18 A-4 C-7 9.7 9.3251 Example 1-19 A-4 C-9 9.7 9.3 249 Example 1-20 A-5 C-1 9.7 9.4 268Example 1-21 A-5 C-2 9.9 9.3 279 Example 1-22 A-5 C-3 10 9.3 301 Example1-23 A-5 C-4 9.9 9.5 342 Example 1-24 A-5 C-6 9.8 9.5 356 Example 1-25A-5 C-7 9.9 9.2 339 Example 1-26 A-5 C-8 9.9 9.3 312 Example 1-27 A-6C-1 9.8 9.3 243 Example 1-28 A-6 C-2 9.7 9.3 228 Example 1-29 A-6 C-39.5 9.4 234 Example 1-30 A-6 C-4 9.7 9.5 255 Example 1-31 A-6 C-5 9.29.7 262 Example 1-32 A-6 C-7 9.5 9.3 261 Example 1-33 A-6 C-8 9.9 9.2226 Example 1-34 A-7 C-1 10.1 7.9 143 Example 1-35 A-7 C-4 9.9 8.4 152Example 1-36 A-7 C-6 9.9 8.2 159 Comparative A-1 C-11 10.1 6.6 121example 1-11 Comparative A-1 C-14 9.5 7.3 104 example 1-12 ComparativeA-1 C-16 10.3 6.8 88 example 1-13 Comparative A-1 C-18 10.1 6.4 109example 1-14 Comparative A-1 C-21 10.3 6.5 92 example 1-15 ComparativeA-1 C-23 10.8 6.1 97 example 1-16 Example 1-37 A-2 C-2 9.9 8.0 198Example 1-38 A-2 C-11 9.5 8.4 232 Example 1-39 A-2 C-12 8.6 9.0 198Example 1-40 A-2 C-13 8.4 9.4 177 Example 1-41 A-2 C-14 8.2 9.8 179Example 1-42 A-2 C-15 8.4 9.2 171 Example 1-43 A-2 C-16 8.9 9.1 167Example 1-44 A-2 C-17 10.0 8.0 210 Example 1-45 A-2 C-18 8.9 8.8 188Example 1-46 A-2 C-21 9.6 8.3 189 Example 1-47 A-2 C-22 8.4 9.1 187Example 1-48 A-2 C-23 9.8 8.0 195 Example 1-49 A-3 C-11 9.5 9.1 158Example 1-50 A-3 C-12 9.1 9.3 138 Example 1-51 A-3 C-13 8.5 9.8 119Example 1-52 A-3 C-14 8.3 10.6 121 Example 1-53 A-3 C-17 10.5 8.3 130Example 1-54 A-3 C-18 9.3 9.1 125 Example 1-55 A-3 C-21 9.6 8.7 126Example 1-56 A-4 C-11 9.5 9.7 286 Example 1-57 A-4 C-12 9.3 9.8 241Example 1-58 A-4 C-13 9.1 10.0 226 Example 1-59 A-4 C-14 8.7 10.8 233Example 1-60 A-4 C-15 8.9 10.5 219 Example 1-61 A-4 C-17 10.1 8.7 233Example 1-62 A-4 C-22 9.2 9.9 234 Example 1-63 A-4 C-23 9.9 9.0 230Example 1-64 A-5 C-11 9.7 9.6 299 Example 1-65 A-5 C-12 9.5 9.8 259Example 1-66 A-5 C-14 9.0 10.8 243 Example 1-67 A-5 C-15 9.2 10.2 231Example 1-68 A-5 C-16 9.4 9.8 228 Example 1-69 A-5 C-18 9.6 9.9 239Example 1-70 A-5 C-21 9.5 9.5 252 Example 1-71 A-5 C-22 9.4 9.8 247Example 1-72 A-6 C-11 9.6 9.6 266 Example 1-73 A-6 C-12 9.3 9.8 222Example 1-74 A-6 C-13 8.6 10.2 205 Example 1-75 A-6 C-14 8.3 10.7 211Example 1-76 A-6 C-15 8.8 10.0 191 Example 1-77 A-6 C-16 9.0 9.9 189Example 1-78 A-6 C-21 9.6 9.5 229 Example 1-79 A-6 C-23 9.9 9.1 237Example 1-80 A-7 C-11 9.7 8.3 167 Example 1-81 A-7 C-12 9.5 8.4 133Example 1-82 A-7 C-14 9.0 9.1 138 Example 1-83 A-7 C-18 9.5 8.3 129Example 1-84 A-7 C-22 9.4 8.6 126 Example 1-85 A-2 C-24 9.8 8.1 178Example 1-86 A-3 C-25 8.5 9.7 135 Example 1-87 A-4 C-26 9.3 9.7 231Example 1-88 A-5 C-24 9.6 9.6 250 Example 1-89 A-5 C-25 9.2 10.2 249Example 1-90 A-6 C-25 9.1 10.2 218 Example 1-91 A-6 C-26 9.4 9.6 216Example 1-92 A-7 C-26 9.5 8.4 131 Example 1-93 A-2 C-27 9.8 8.0 186Example 1-94 A-3 C-28 9.3 9.1 123 Example 1-95 A-4 C-29 9.0 10.1 217Example 1-96 A-5 C-27 9.9 9.1 256 Example 1-97 A-5 C-28 9.6 9.8 240Example 1-98 A-6 C-27 9.6 9.2 221 Example 1-99 A-6 C-29 8.6 9.3 216Example 1-100 A-7 C-28 9.6 8.3 127 Example 1-101 A-2 C-30 9.6 8.5 232Example 1-102 A-2 C-32 9.5 8.6 208 Example 1-103 A-2 C-34 9.6 8.3 214Example 1-104 A-2 C-36 9.2 9.0 174 Example 1-105 A-2 C-38 9.2 9.1 179Example 1-106 A-2 C-39 9.0 9.5 165 Example 1-107 A-2 C-40 9.5 8.6 226Example 1-108 A-2 C-42 9.2 9.5 183 Example 1-109 A-3 C-30 9.8 8.6 150Example 1-110 A-3 C-31 9.6 9.3 136 Example 1-111 A-3 C-33 9.7 8.6 125Example 1-112 A-3 C-34 10.0 8.4 133 Example 1-113 A-3 C-35 9.7 8.8 122Example 1-114 A-3 C-37 9.0 9.7 119 Example 1-115 A-3 C-39 9.2 9.5 116Example 1-116 A-3 C-41 9.4 9.2 119 Example 1-117 A-4 C-30 10.1 9.2 289Example 1-118 A-4 C-31 9.7 9.8 258 Example 1-119 A-4 C-32 10.0 9.3 244Example 1-120 A-4 C-33 10.0 9.1 233 Example 1-121 A-4 C-34 10.2 9.1 248Example 1-122 A-4 C-35 9.9 9.5 230 Example 1-123 A-4 C-36 9.5 9.9 217Example 1-124 A-4 C-37 9.3 10.3 212 Example 1-125 A-4 C-38 9.5 9.9 219Example 1-126 A-4 C-39 9.6 10.3 207 Example 1-127 A-4 C-40 9.6 9.4 283Example 1-128 A-4 C-41 9.5 9.5 213 Example 1-129 A-4 C-42 9.4 10.0 217Example 1-130 A-5 C-30 10.1 9.3 331 Example 1-131 A-5 C-31 9.6 9.8 305Example 1-132 A-5 C-32 9.9 9.5 292 Example 1-133 A-5 C-33 9.8 9.4 272Example 1-134 A-5 C-34 10.1 9.2 289 Example 1-135 A-5 C-35 9.9 9.6 270Example 1-136 A-5 C-36 9.4 9.8 243 Example 1-137 A-5 C-37 9.2 10.2 235Example 1-138 A-5 C-38 9.3 10.1 239 Example 1-139 A-5 C-39 9.8 10.6 221Example 1-140 A-5 C-40 9.9 9.2 298 Example 1-141 A-5 C-41 9.6 9.7 223Example 1-142 A-5 C-42 9.4 10.3 246 Example 1-143 A-6 C-30 9.9 9.6 245Example 1-144 A-6 C-31 9.5 9.8 229 Example 1-145 A-6 C-32 9.8 9.6 216Example 1-146 A-6 C-35 9.6 9.8 202 Example 1-147 A-6 C-36 9.2 10.1 187Example 1-148 A-6 C-39 9.3 10.7 176 Example 1-149 A-6 C-40 9.9 9.6 220Example 1-150 A-7 C-30 9.9 8.2 149 Example 1-151 A-7 C-33 9.8 8.4 135Example 1-152 A-7 C-34 9.8 8.1 140 Example 1-153 A-7 C-37 9.0 9.0 124Example 1-154 A-7 C-38 9.2 8.8 129 Example 1-155 A-7 C-41 9.4 8.6 122Example 1-156 A-7 C-42 9.1 8.8 130 Example 1-157 A-2 C-46 9.3 9.0 223Example 1-158 A-2 C-48 9.0 9.2 220 Example 1-159 A-2 C-51 9.8 8.1 231Example 1-160 A-2 C-53 9.7 8.2 239 Example 1-161 A-2 C-55 9.7 8.2 226Example 1-162 A-3 C-47 9.4 9.0 132 Example 1-163 A-3 C-49 8.9 9.5 127Example 1-164 A-3 C-52 9.7 8.7 147 Example 1-165 A-3 C-54 9.3 9.2 134Example 1-166 A-3 C-56 9.1 9.3 115 Example 1-167 A-4 C-46 9.6 9.8 238Example 1-168 A-4 C-47 9.8 9.4 216 Example 1-169 A-4 C-48 9.2 10.0 224Example 1-170 A-4 C-49 9.1 9.9 208 Example 1-171 A-4 C-51 9.8 8.7 236Example 1-172 A-4 C-52 9.8 8.8 234 Example 1-173 A-4 C-53 9.8 9.0 245Example 1-174 A-4 C-54 9.6 9.6 211 Example 1-175 A-4 C-55 9.7 9.2 230Example 1-176 A-4 C-56 9.2 9.8 198 Example 1-177 A-5 C-46 9.5 9.8 291Example 1-178 A-5 C-47 9.7 9.6 273 Example 1-179 A-5 C-48 9.3 10.0 287Example 1-180 A-5 C-49 9.2 10.0 262 Example 1-181 A-5 C-51 9.9 9.1 298Example 1-182 A-5 C-52 9.8 9.3 303 Example 1-183 A-5 C-53 9.7 9.4 288Example 1-184 A-5 C-54 9.6 9.7 259 Example 1-185 A-5 C-55 9.8 9.5 283Example 1-186 A-5 C-56 9.3 9.7 238 Example 1-187 A-6 C-46 9.3 9.7 240Example 1-188 A-6 C-47 9.4 9.5 227 Example 1-189 A-6 C-51 9.6 9.0 241Example 1-190 A-6 C-52 9.6 9.2 238 Example 1-191 A-6 C-55 9.5 9.4 229Example 1-192 A-6 C-56 8.8 9.9 200 Example 1-193 A-7 C-46 9.6 8.7 144Example 1-194 A-7 C-48 9.4 9.1 137 Example 1-195 A-7 C-49 9.3 9.1 129Example 1-196 A-7 C-51 10.0 8.0 145 Example 1-197 A-7 C-54 9.6 8.6 131Example 1-198 A-7 C-55 9.9 8.1 134

As apparent from the above results, the device of the present inventionhad higher external quantum efficiency and lower driving voltage thanthe comparative devices. In particular, high durability was shown whendriving at a high temperature (70° C.).

Example 2 Comparative Example 2-1

An organic EL device in Comparative Example 2-1 was manufactured in thesame manner as in Comparative Example 1-1, except that vapor depositionwas performed by changing a composition ratio of the film of the lightemitting layer from 9:91 (mass ratio) of A-1 to C-1 in ComparativeExample 1-1 to 5:95 (mass ratio) of B-1 to C-1 (film thickness: 30 nm).A direct current constant voltage was applied to the organic EL deviceto emit light by means of a source measure unit Model 2400 manufacturedby Toyo Technica, and as a result, light emission derived from B-1 couldbe obtained.

Examples 2-1 to 2-249 and Comparative Examples 2-2 to 2-15

Devices in Examples 2-1 to 2-249 and Comparative Examples 2-2 to 2-15were manufactured in the same manner as in Comparative Example 2-1,except that the materials used in Comparative Example 2-1 were changedinto the materials described in Table 2. A direct current constantvoltage was applied to the organic EL device to emit light by means of asource measure unit Model 2400 manufactured by Toyo Technica, and as aresult, a light emission of color derived from each light emittingmaterial could be obtained.

The devices thus-obtained above were evaluated in the same manner as inExample 1.

TABLE 2 Half-luminance Light emitting intensity time layer External(relative value) at an Light Driving quantum ambient air emitting Hostvoltage (V) at efficiency (%) temperature of 70° C. material material1000 cd/m² at 1000 cd/m² and 1000 cd/m² Comparative B-1 C-1 11.1 5.3 100example 2-1 Comparative B-1 C-3 11.3 5.4 104 example 2-2 Comparative B-1C-6 11.2 5.3 110 example 2-3 Comparative B-1 C-9 11.4 5.1 108 example2-4 Comparative B-1 H-1 10.8 5.6 96 example 2-5 Comparative B-3 H-1 10.65.8 185 example 2-6 Comparative B-6 H-1 10.5 5.7 176 example 2-7Comparative B-8 H-1 10.4 5.5 153 example 2-8 Example 2-1 B-2 C-1 10.36.1 239 Example 2-2 B-2 C-3 10.5 6.3 243 Example 2-3 B-2 C-6 10.3 6.2266 Example 2-4 B-2 C-9 10.5 6.1 233 Example 2-5 B-3 C-1 10.7 6.3 253Example 2-6 B-3 C-3 10.8 6.4 264 Example 2-7 B-3 C-4 10.7 6.6 275Example 2-8 B-3 C-6 10.5 6.4 271 Example 2-9 B-3 C-7 10.6 6.5 264Example 2-10 B-3 C-8 10.9 6.2 234 Example 2-11 B-4 C-2 10.6 6.5 265Example 2-12 B-4 C-3 10.7 6.4 276 Example 2-13 B-4 C-5 10.1 6.9 253Example 2-14 B-4 C-6 10.6 6.4 294 Example 2-15 B-4 C-7 10.5 6.5 301Example 2-16 B-4 C-9 10.8 6.3 278 Example 2-17 B-5 C-1 10.3 6.1 223Example 2-18 B-5 C-2 10.4 6.3 235 Example 2-19 B-5 C-3 10.3 6.5 253Example 2-20 B-5 C-6 10.5 6.2 272 Example 2-21 B-5 C-8 10.7 6.1 211Example 2-22 B-6 C-1 10.1 6.3 288 Example 2-23 B-6 C-3 10 6.4 273Example 2-24 B-6 C-4 10.3 6.5 298 Example 2-25 B-6 C-6 10.2 6.2 285Example 2-27 B-6 C-7 10.3 6.2 301 Example 2-28 B-7 C-1 10.4 6.2 242Example 2-29 B-7 C-3 10.4 6.3 261 Example 2-30 B-7 C-4 10.4 6.4 279Example 2-31 B-7 C-6 10.2 6.3 280 Example 2-32 B-7 C-8 10.4 6.2 251Example 2-33 B-8 C-1 10.2 6.1 241 Example 2-34 B-8 C-2 10.3 6.2 235Example 2-35 B-8 C-6 10.1 6.4 253 Example 2-36 B-8 C-8 10.1 6.3 278Example 2-37 B-8 C-9 10.4 6.1 239 Example 2-38 B-9 C-1 10.6 6.3 234Example 2-39 B-9 C-2 10.4 6.3 237 Example 2-40 B-9 C-4 10.4 6.3 251Example 2-41 B-9 C-7 10.5 6.2 263 Comparative B-1 C-11 10.9 5.4 118example 2-9 Comparative B-1 C-14 10.6 5.7 87 example 2-10 ComparativeB-1 C-18 11.0 5.4 86 example 2-11 Comparative B-1 C-19 10.3 5.8 92example 2-12 Comparative B-1 C-20 10.2 5.8 109 example 2-13 ComparativeB-1 C-21 10.9 5.4 93 example 2-14 Comparative B-1 C-22 10.8 5.5 81example 2-15 Example 2-42 B-2 C-11 10.1 6.3 262 Example 2-43 B-2 C-129.8 6.4 213 Example 2-44 B-2 C-14 9.3 6.8 228 Example 2-45 B-2 C-15 9.66.5 221 Example 2-46 B-2 C-19 9.4 6.6 252 Example 2-47 B-2 C-20 9.2 7.2286 Example 2-48 B-2 C-22 9.7 6.5 205 Example 2-49 B-2 C-23 10.4 6.0 234Example 2-50 B-3 C-11 10.5 6.5 281 Example 2-51 B-3 C-13 10.0 6.8 219Example 2-52 B-3 C-14 9.8 7.1 236 Example 2-53 B-3 C-15 9.9 6.7 201Example 2-54 B-3 C-16 10.3 6.5 208 Example 2-55 B-3 C-19 9.8 7.1 233Example 2-56 B-3 C-20 9.6 7.4 297 Example 2-57 B-3 C-21 10.5 6.4 240Example 2-58 B-3 C-23 10.9 6.2 249 Example 2-59 B-4 C-11 10.3 6.8 296Example 2-60 B-4 C-13 9.7 7.2 230 Example 2-61 B-4 C-14 9.4 7.5 244Example 2-62 B-4 C-18 10.0 7.1 216 Example 2-63 B-4 C-19 9.5 7.1 241Example 2-64 B-4 C-20 9.4 7.6 309 Example 2-65 B-4 C-21 10.5 6.5 249Example 2-66 B-4 C-22 9.7 7.1 215 Example 2-67 B-5 C-11 10.0 6.4 255Example 2-68 B-5 C-14 9.3 7.5 219 Example 2-69 B-5 C-17 10.8 5.8 217Example 2-70 B-5 C-19 9.4 7.4 210 Example 2-71 B-5 C-20 9.2 7.7 268Example 2-72 B-5 C-22 9.7 6.7 199 Example 2-73 B-5 C-23 10.4 6.0 217Example 2-74 B-6 C-11 9.8 6.4 313 Example 2-75 B-6 C-12 9.9 6.5 258Example 2-76 B-6 C-14 9.2 7.5 264 Example 2-77 B-6 C-15 9.7 6.8 238Example 2-78 B-6 C-19 9.3 7.5 256 Example 2-79 B-6 C-20 9.1 7.4 281Example 2-80 B-6 C-21 10.0 6.2 281 Example 2-81 B-6 C-23 10.3 6.2 282Example 2-82 B-7 C-11 10.3 6.4 266 Example 2-83 B-7 C-13 9.8 7.2 203Example 2-84 B-7 C-14 9.5 7.5 229 Example 2-85 B-7 C-16 10.0 6.9 191Example 2-86 B-7 C-19 9.6 7.3 224 Example 2-87 B-7 C-20 9.5 7.3 275Example 2-88 B-7 C-21 10.2 6.2 230 Example 2-89 B-7 C-22 9.8 7.1 195Example 2-90 B-8 C-11 10.0 6.2 266 Example 2-91 B-8 C-14 9.3 7.5 228Example 2-92 B-8 C-17 10.9 5.7 236 Example 2-93 B-8 C-19 9.4 7.3 219Example 2-94 B-8 C-20 9.2 7.6 273 Example 2-95 B-8 C-22 9.9 6.7 199Example 2-96 B-8 C-23 10.3 6.2 232 Example 2-97 B-9 C-11 10.4 6.5 266Example 2-98 B-9 C-12 10.2 6.7 197 Example 2-99 B-9 C-14 9.3 7.7 219Example 2-100 B-9 C-18 10.2 6.5 189 Example 2-101 B-9 C-19 9.4 7.5 214Example 2-102 B-9 C-20 9.3 7.6 281 Example 2-103 B-9 C-21 10.3 6.4 222Example 2-104 B-9 C-23 10.6 6.1 228 Example 2-105 B-2 C-24 9.8 6.2 211Example 2-106 B-3 C-25 9.6 7.3 243 Example 2-107 B-4 C-26 10.1 6.7 227Example 2-108 B-5 C-24 10.0 6.6 221 Example 2-109 B-6 C-25 9.7 7.0 250Example 2-110 B-7 C-26 10.0 6.2 229 Example 2-111 B-8 C-25 9.8 6.8 196Example 2-112 B-9 C-24 10.3 6.5 212 Example 2-113 B-2 C-29 9.7 6.5 198Example 2-114 B-3 C-28 10.0 6.7 208 Example 2-115 B-4 C-27 10.7 6.4 246Example 2-116 B-5 C-29 9.9 6.7 188 Example 2-117 B-6 C-28 10.1 6.4 241Example 2-118 B-7 C-27 10.2 6.1 222 Example 2-119 B-8 C-29 10.1 6.7 183Example 2-120 B-9 C-27 10.6 6.1 226 Example 2-121 B-2 C-30 10.5 6.3 251Example 2-122 B-2 C-32 10.3 6.4 225 Example 2-123 B-2 C-34 10.6 6.2 223Example 2-124 B-2 C-36 9.8 6.9 201 Example 2-125 B-2 C-38 9.8 6.8 208Example 2-126 B-2 C-39 10.0 7.3 196 Example 2-127 B-2 C-40 10.6 6.3 238Example 2-128 B-2 C-42 9.9 6.9 210 Example 2-129 B-3 C-30 10.8 6.5 262Example 2-130 B-3 C-31 10.3 6.9 236 Example 2-131 B-3 C-33 10.6 6.6 229Example 2-132 B-3 C-34 10.9 6.3 241 Example 2-133 B-3 C-35 10.5 6.7 230Example 2-134 B-3 C-37 9.7 7.6 202 Example 2-135 B-3 C-39 10.0 7.9 197Example 2-136 B-3 C-41 10.1 7.3 208 Example 2-137 B-4 C-30 10.8 6.3 291Example 2-138 B-4 C-31 10.2 6.7 265 Example 2-139 B-4 C-32 10.7 6.4 258Example 2-140 B-4 C-33 10.7 6.3 244 Example 2-141 B-4 C-34 10.9 6.2 267Example 2-142 B-4 C-35 10.6 6.5 253 Example 2-143 B-4 C-36 10.1 6.9 229Example 2-144 B-4 C-37 9.8 7.3 217 Example 2-145 B-4 C-38 9.9 7.2 225Example 2-146 B-4 C-39 10.0 7.5 210 Example 2-147 B-4 C-40 10.9 6.3 270Example 2-148 B-4 C-41 10.3 6.9 213 Example 2-149 B-4 C-42 10.0 7.3 234Example 2-150 B-5 C-30 10.8 6.4 266 Example 2-151 B-5 C-31 10.3 6.7 243Example 2-152 B-5 C-34 10.9 6.2 245 Example 2-153 B-5 C-35 10.3 6.6 232Example 2-154 B-5 C-38 9.9 6.9 230 Example 2-155 B-5 C-39 9.9 7.4 203Example 2-156 B-6 C-30 10.4 6.3 286 Example 2-157 B-6 C-31 9.9 6.6 266Example 2-158 B-6 C-32 10.3 6.4 254 Example 2-159 B-6 C-33 10.4 6.3 245Example 2-160 B-6 C-34 10.5 6.2 260 Example 2-161 B-6 C-35 10.0 6.6 245Example 2-162 B-6 C-36 9.7 6.8 222 Example 2-163 B-6 C-37 9.4 7.4 214Example 2-164 B-6 C-38 9.6 7.0 233 Example 2-165 B-6 C-39 9.7 7.6 208Example 2-166 B-6 C-40 10.4 6.2 271 Example 2-167 B-6 C-41 10.0 6.5 224Example 2-168 B-6 C-42 9.8 7.0 229 Example 2-169 B-7 C-30 10.5 6.3 273Example 2-170 B-7 C-32 10.3 6.4 248 Example 2-171 B-7 C-33 10.4 6.4 236Example 2-172 B-7 C-36 9.8 6.9 211 Example 2-173 B-7 C-37 9.5 7.5 213Example 2-174 B-7 C-40 10.5 6.2 260 Example 2-175 B-7 C-41 10.2 6.5 223Example 2-176 B-8 C-30 10.3 6.1 239 Example 2-177 B-8 C-33 10.3 6.2 210Example 2-178 B-8 C-34 10.4 6.0 219 Example 2-179 B-8 C-37 9.3 7.2 188Example 2-180 B-8 C-38 9.6 6.9 204 Example 2-181 B-8 C-41 10.2 6.4 197Example 2-182 B-8 C-42 10.0 6.7 207 Example 2-183 B-9 C-30 10.5 6.2 243Example 2-184 B-9 C-31 10.2 6.4 224 Example 2-185 B-9 C-32 10.4 6.3 218Example 2-186 B-9 C-33 10.5 6.1 212 Example 2-187 B-9 C-37 9.6 7.3 185Example 2-188 B-9 C-38 9.9 7.0 201 Example 2-189 B-9 C-39 9.9 7.5 181Example 2-190 B-2 C-46 9.8 6.5 241 Example 2-191 B-2 C-48 9.5 6.7 237Example 2-192 B-2 C-50 9.2 6.9 277 Example 2-193 B-2 C-52 10.5 6.0 239Example 2-194 B-2 C-54 9.8 6.6 211 Example 2-195 B-2 C-56 9.3 6.7 200Example 2-196 B-3 C-46 9.9 6.7 244 Example 2-197 B-3 C-47 10.1 6.5 233Example 2-198 B-3 C-49 9.8 6.8 223 Example 2-199 B-3 C-51 10.6 6.3 245Example 2-200 B-3 C-53 10.3 6.4 251 Example 2-201 B-3 C-55 10.3 6.6 250Example 2-202 B-4 C-46 9.7 6.7 273 Example 2-203 B-4 C-47 10.1 6.3 250Example 2-204 B-4 C-48 9.4 6.9 261 Example 2-205 B-4 C-49 9.3 6.8 238Example 2-206 B-4 C-50 9.3 7.3 295 Example 2-207 B-4 C-51 10.7 6.2 275Example 2-208 B-4 C-52 10.6 6.4 273 Example 2-209 B-4 C-53 10.5 6.4 279Example 2-210 B-4 C-54 9.9 6.5 238 Example 2-211 B-4 C-55 10.3 6.4 262Example 2-212 B-4 C-56 9.5 6.7 222 Example 2-213 B-5 C-46 10.1 6.8 251Example 2-214 B-5 C-47 10.3 6.4 229 Example 2-215 B-5 C-50 9.6 7.1 233Example 2-216 B-5 C-51 10.6 6.0 248 Example 2-217 B-5 C-54 10.1 6.5 223Example 2-218 B-5 C-55 10.4 6.2 244 Example 2-219 B-6 C-46 9.8 6.8 266Example 2-220 B-6 C-47 10.0 6.4 245 Example 2-221 B-6 C-48 9.5 7.1 260Example 2-222 B-6 C-49 9.5 7.1 233 Example 2-223 B-6 C-50 9.4 7.5 288Example 2-224 B-6 C-51 10.3 6.0 262 Example 2-225 B-6 C-52 10.2 6.1 266Example 2-226 B-6 C-53 10.2 6.3 272 Example 2-227 B-6 C-54 10.0 6.7 232Example 2-228 B-6 C-55 10.1 6.4 258 Example 2-229 B-6 C-56 9.8 7.0 210Example 2-230 B-7 C-46 9.9 6.8 255 Example 2-231 B-7 C-48 9.7 7.1 244Example 2-232 B-7 C-49 9.8 7.1 221 Example 2-233 B-7 C-50 9.6 7.5 280Example 2-234 B-7 C-52 10.2 6.1 257 Example 2-235 B-7 C-53 10.0 6.5 261Example 2-236 B-7 C-56 9.8 6.9 209 Example 2-237 B-8 C-46 9.8 6.8 235Example 2-238 B-8 C-47 10.0 6.5 219 Example 2-239 B-8 C-48 9.5 7.1 227Example 2-240 B-8 C-52 10.2 6.2 238 Example 2-241 B-8 C-53 10.2 6.3 234Example 2-242 B-8 C-54 9.9 6.6 205 Example 2-243 B-9 C-46 9.9 6.8 240Example 2-244 B-9 C-48 9.6 7.3 241 Example 2-245 B-9 C-49 9.4 7.5 223Example 2-246 B-9 C-50 9.5 7.7 280 Example 2-247 B-9 C-54 10.1 6.7 222Example 2-248 B-9 C-55 10.5 6.4 229 Example 2-249 B-9 C-56 9.6 6.7 207

As apparent from the above results, the device of the present inventionhad higher external quantum efficiency and lower driving voltage thanthe comparative devices. In particular, high durability was shown whendriving at a high temperature (70° C.).

Example 3

Comparative Example 3-1

A glass substrate having an ITO film having a thickness of 0.5 mm andeach side of 2.5 cm in square (manufactured by Geomatec Co., Ltd., andsurface resistance 10Ω/□) was put into a washing container,ultrasonically washed in 2-propanol, followed by UV-ozone treatment for30 min. A solution ofpoly(3,4-ethylenedioxythiophene)-polystyrenesulfonate

(PEDOT/PSS) diluted with pure water in an amount of 70% by mass wascoated on this by using a spin coater to provide a hole transportinglayer having a thickness of 50 nm. A methylene chloride solution inwhich A-1 and C-1 were dissolved in a ratio of 4:96 (mass ratio) wascoated by using a spin coater to obtain a light emitting layer having athickness of 30 nm. Thereon, BAlq[bis-(2-methyl-8-quinolinolate)-4-(phenylphenolate)aluminum] wasvapor-deposited to a thickness of 40 nm. Thereon, lithium chloride as acathode buffer layer and aluminum as a cathode were vapor-deposited tothicknesses of 0.5 nm and 150 nm, respectively, in a vapor depositionapparatus. This was placed in a glove box substituted with argon gas soas not to be exposed to the atmosphere and sealed using a stainlesssteel-made sealing tube and a UV-curable adhesive (XNR5516HV,manufactured by Nagase-CHIBA Ltd.) to manufacture an organic EL devicein Comparative Example 3-1. A direct current constant voltage wasapplied to the organic EL device to emit light by means of a sourcemeasure unit Model 2400 manufactured by Toyo Technica, and as a result,light emission derived from A-1 could be obtained.

Examples 3-1 to 3-133 and Comparative Examples 3-2 to 3-7

Devices in Examples 3-1 to 3-133 and Comparative Examples 3-2 to 3-7were manufactured in the same manner as in Comparative Example 3-1,except that the materials used in Comparative Example 3-1 were changedinto the materials described in Table 3. A direct current constantvoltage was applied to the organic EL device to emit light by means of asource measure unit Model 2400 manufactured by Toyo Technica, and as aresult, a light emission of color derived from each light emittingmaterial could be obtained.

The devices thus-obtained above were evaluated in the same manner as inExample 1.

TABLE 3 Light emitting Half-luminance intensity layer External time(relative value) at Light Driving quantum an ambient air emitting Hostvoltage (V) at efficiency (%) temperature of 70° C. and materialmaterial 1000 cd/m² at 1000 cd/m² 1000 cd/m² Comparative A-1 C-1 14.33.2 100 example 3-1 Comparative A-1 C-3 14.9 2.9 92 example 3-2Comparative A-1 C-10 15.6 2.8 83 example 3-3 Comparative A-1 H-1 14.52.8 131 example 3-4 Comparative A-5 H-1 13.8 3.8 183 example 3-5 Example3-1 A-2 C-1 13.6 5.1 215 Example 3-2 A-2 C-3 13.7 4.9 242 Example 3-3A-2 C-6 13.6 4.9 259 Example 3-4 A-2 C-10 14.0 4.7 208 Example 3-5 A-3C-1 13.6 5.3 239 Example 3-6 A-3 C-2 13.7 5.4 247 Example 3-7 A-3 C-913.5 5.3 232 Example 3-8 A-3 C-10 13.9 5.1 209 Example 3-9 A-4 C-2 13.45.8 258 Example 3-10 A-4 C-3 13.6 5.7 261 Example 3-11 A-4 C-6 13.4 5.7283 Example 3-12 A-4 C-8 13.7 5.6 239 Example 3-13 A-5 C-1 13.3 5.6 259Example 3-14 A-5 C-6 13.8 5.3 366 Example 3-15 A-5 C-9 13.5 5.5 261Example 3-16 A-5 C-10 14.1 5.1 223 Example 3-130 A-6 C-1 13.3 5.7 249Example 3-131 A-6 C-4 13.5 5.5 276 Example 3-132 A-6 C-9 13.4 5.6 281Example 3-133 A-6 C-10 14.2 5.0 209 Comparative A-1 C-14 13.5 3.7 94example 3-6 Comparative A-1 C-21 14.3 3.3 91 example 3-7 Example 3-17A-2 C-11 13.4 5.3 239 Example 3-18 A-2 C-14 12.2 6.0 201 Example 3-19A-2 C-15 12.4 5.8 188 Example 3-20 A-2 C-22 13.3 5.4 179 Example 3-21A-3 C-11 13.4 5.5 261 Example 3-22 A-3 C-12 13.1 5.7 197 Example 3-23A-3 C-14 12.3 6.5 220 Example 3-24 A-3 C-16 13.3 5.7 193 Example 3-25A-3 C-18 13.2 5.6 188 Example 3-26 A-3 C-21 13.0 5.8 192 Example 3-27A-4 C-11 13.2 6.0 275 Example 3-28 A-4 C-13 12.5 6.6 231 Example 3-29A-4 C-14 12.2 6.9 244 Example 3-30 A-4 C-17 13.6 5.7 260 Example 3-31A-4 C-23 13.6 5.6 239 Example 3-32 A-5 C-11 13.1 5.8 283 Example 3-33A-5 C-12 12.9 5.8 217 Example 3-34 A-5 C-14 12.1 6.7 243 Example 3-35A-5 C-18 13.0 5.7 208 Example 3-36 A-5 C-21 13.0 5.8 245 Example 3-37A-6 C-11 13.0 5.9 277 Example 3-38 A-6 C-13 12.3 6.5 216 Example 3-39A-6 C-14 12.0 6.9 232 Example 3-40 A-6 C-15 12.2 6.7 218 Example 3-41A-6 C-18 12.7 6.1 208 Example 3-42 A-6 C-22 12.4 6.5 203 Example 3-43A-4 C-24 13.0 6.2 240 Example 3-44 A-5 C-25 12.5 6.3 208 Example 3-45A-6 C-26 12.7 6.1 233 Example 3-46 A-2 C-27 13.7 5.2 207 Example 3-47A-3 C-28 13.3 5.6 186 Example 3-48 A-4 C-27 13.5 5.7 244 Example 3-49A-4 C-29 12.5 6.2 210 Example 3-50 A-5 C-28 12.8 6.0 209 Example 3-51A-6 C-27 13.5 5.5 233 Example 3-52 A-2 C-30 13.8 5.0 238 Example 3-53A-2 C-32 13.6 5.1 218 Example 3-54 A-2 C-34 13.7 5.1 221 Example 3-55A-2 C-36 13.1 5.4 187 Example 3-56 A-2 C-38 13.0 5.5 193 Example 3-57A-2 C-43 12.8 5.6 180 Example 3-58 A-2 C-44 13.9 5.2 212 Example 3-59A-3 C-30 13.6 5.3 237 Example 3-60 A-3 C-31 13.2 5.6 215 Example 3-61A-3 C-33 13.5 5.3 204 Example 3-62 A-3 C-34 13.5 5.2 219 Example 3-63A-3 C-35 13.2 5.5 210 Example 3-64 A-3 C-37 12.5 6.2 197 Example 3-65A-3 C-39 12.2 6.6 192 Example 3-66 A-3 C-45 13.2 5.8 211 Example 3-67A-4 C-30 13.5 5.7 263 Example 3-68 A-4 C-32 13.4 5.8 237 Example 3-69A-4 C-33 13.4 5.7 228 Example 3-70 A-4 C-36 12.9 6.2 213 Example 3-71A-4 C-40 13.6 5.6 255 Example 3-72 A-4 C-41 13.2 5.9 224 Example 3-73A-4 C-43 12.7 6.3 217 Example 3-74 A-4 C-45 13.1 6.1 219 Example 3-75A-5 C-30 13.6 5.5 288 Example 3-76 A-5 C-34 13.5 5.5 273 Example 3-77A-5 C-35 13.2 5.8 265 Example 3-78 A-5 C-38 12.9 6.0 244 Example 3-79A-5 C-39 12.8 6.6 229 Example 3-80 A-5 C-42 13.2 5.9 240 Example 3-81A-5 C-44 13.7 5.7 261 Example 3-82 A-5 C-45 13.2 5.9 259 Example 3-83A-6 C-30 13.4 5.5 265 Example 3-84 A-6 C-31 12.9 5.8 240 Example 3-85A-6 C-32 13.2 5.6 233 Example 3-86 A-6 C-37 12.3 6.5 214 Example 3-87A-6 C-40 13.4 5.6 256 Example 3-88 A-6 C-41 12.5 5.8 228 Example 3-89A-6 C-42 12.2 6.2 233 Example 3-90 A-6 C-43 12.3 6.1 213 Example 3-91A-6 C-45 12.6 5.8 221 Example 3-92 A-2 C-46 13.2 5.3 235 Example 3-93A-2 C-48 12.8 5.7 228 Example 3-94 A-2 C-49 12.7 5.8 209 Example 3-95A-2 C-52 13.6 4.8 232 Example 3-96 A-2 C-54 13.3 5.2 224 Example 3-97A-2 C-57 13.4 5.0 246 Example 3-98 A-2 C-58 13.0 5.4 221 Example 3-99A-3 C-46 13.3 5.5 247 Example 3-100 A-3 C-47 13.5 5.2 224 Example 3-101A-3 C-49 13.0 5.8 209 Example 3-102 A-3 C-51 13.7 5.1 243 Example 3-103A-3 C-53 13.6 5.2 229 Example 3-104 A-3 C-55 13.6 5.4 233 Example 3-105A-3 C-57 13.5 5.2 255 Example 3-106 A-3 C-59 13.5 5.4 228 Example 3-107A-4 C-46 12.8 6.1 266 Example 3-108 A-4 C-48 12.4 6.5 254 Example 3-109A-4 C-49 12.5 6.5 236 Example 3-110 A-4 C-52 13.6 5.5 261 Example 3-111A-4 C-53 13.4 5.6 268 Example 3-112 A-4 C-56 12.6 6.3 213 Example 3-113A-4 C-58 13.3 6.2 255 Example 3-114 A-4 C-59 13.5 5.7 262 Example 3-115A-5 C-46 13.0 6.1 313 Example 3-116 A-5 C-48 12.7 6.4 307 Example 3-117A-5 C-49 12.5 6.5 261 Example 3-118 A-5 C-51 13.9 5.2 312 Example 3-119A-5 C-54 13.1 6.0 259 Example 3-120 A-5 C-57 13.5 5.5 341 Example 3-121A-5 C-58 12.9 6.2 288 Example 3-122 A-6 C-46 13.1 5.9 270 Example 3-123A-6 C-48 12.6 6.3 256 Example 3-124 A-6 C-49 12.5 6.3 231 Example 3-125A-6 C-52 13.5 5.4 267 Example 3-126 A-6 C-53 13.3 5.5 269 Example 3-127A-6 C-54 13.1 5.9 242 Example 3-128 A-6 C-58 13.0 6.0 258 Example 3-129A-6 C-59 13.3 5.6 271

As apparent from the above results, the device of the present inventionhad higher external quantum efficiency and lower driving voltage thancomparative devices. In particular, high durability was shown whendriving at a high temperature (70° C.). Example 3 exemplifies themanufacture of a light emitting layer by coating, and is excellent interms of manufacturing costs.

Example 4 Comparative Example 4-1

An organic EL device in Comparative Example 4-1 was manufactured in thesame manner as in Comparative Example 3-1, except that vapor depositionwas performed by changing a composition of the film of the lightemitting layer from 4:96 (mass ratio) of A-1 to C-1 in ComparativeExample 3-1 to 4:96 (mass ratio) of B-1 to C-1 (film thickness: 30 nm).A direct current constant voltage was applied to the organic EL deviceto emit light by means of a source measure unit Model 2400 manufacturedby Toyo Technica, and as a result, light emission derived from B-1 couldbe obtained.

Examples 4-1 to 4-184 and Comparative Examples 4-2 to 4-9

Devices in Examples 4-1 to 4-184 and Comparative Examples 4-2 to 4-9were manufactured in the same manner as in Comparative Example 4-1,except that the materials used in Comparative Example 4-1 were changedinto the materials described in Table 4. A direct current constantvoltage was applied to the organic EL device to emit light by means of asource measure unit Model 2400 manufactured by Toyo Technica, and as aresult, a light emission of color derived from each light emittingmaterial could be obtained.

The devices thus-obtained above were evaluated in the same manner as inExample 1.

TABLE 4 Light emitting layer External Half-luminance intensity LightDriving quantum time (relative value) at an emitting Host voltage (V) atefficiency (%) ambient air temperature of material material 1000 cd/m²at 1000 cd/m² 70° C. and 1000 cd/m² Comparative B-1 C-1 15.4 2.2 100example 4-1 Comparative B-1 C-6 15.6 2.4 117 example 4-2 Comparative B-1C-9 15.5 2.4 94 example 4-3 Comparative B-1 C-10 16.4 1.9 79 example 4-4Comparative B-1 H-1 15.1 2.4 98 example 4-5 Comparative B-6 H-1 14.8 2.5165 example 4-6 Example 4-1 B-2 C-1 14.6 3.0 251 Example 4-2 B-2 C-314.8 3.1 258 Example 4-3 B-2 C-7 14.7 3.0 289 Example 4-4 B-2 C-10 15.42.8 219 Example 4-5 B-3 C-1 15.1 3.1 267 Example 4-6 B-3 C-6 14.9 3.2278 Example 4-5 B-3 C-8 15.1 3.0 241 Example 4-6 B-3 C-9 15.1 3.1 273Example 4-7 B-4 C-2 14.9 3.3 273 Example 4-8 B-4 C-6 15.0 3.4 302Example 4-9 B-4 C-7 15.1 3.4 313 Example 4-10 B-4 C-10 15.6 3.0 238Example 4-11 B-5 C-1 15.0 3.3 246 Example 4-12 B-5 C-6 15.2 3.1 281Example 4-13 B-5 C-7 15.3 3.2 279 Example 4-14 B-5 C-10 16.0 2.9 222Example 4-15 B-6 C-1 14.7 3.1 302 Example 4-16 B-6 C-6 14.9 3.1 297Example 4-17 B-6 C-9 14.7 3.0 281 Example 4-18 B-6 C-10 15.8 2.7 231Example 4-19 B-7 C-1 15.0 3.3 259 Example 4-20 B-7 C-6 15.2 3.1 287Example 4-21 B-7 C-9 15.1 3.2 245 Example 4-22 B-7 C-10 15.8 2.8 211Example 4-23 B-9 C-1 15.2 3.0 248 Example 4-24 B-9 C-7 15.2 3.1 271Example 4-25 B-9 C-10 15.8 2.8 222 Comparative B-1 C-11 15.2 2.3 112example 4-7 Comparative B-1 C-14 14.8 2.8 85 example 4-8 Comparative B-1C-20 14.7 2.9 119 example 4-9 Example 4-26 B-2 C-11 14.3 3.3 272 Example4-27 B-2 C-12 13.9 3.4 211 Example 4-28 B-2 C-14 12.8 4.4 231 Example4-29 B-2 C-15 13.0 4.2 219 Example 4-30 B-2 C-18 14.0 3.4 205 Example4-31 B-2 C-20 12.6 4.6 283 Example 4-32 B-2 C-21 14.3 3.2 237 Example4-33 B-3 C-11 14.7 3.4 282 Example 4-34 B-3 C-13 13.9 4.1 239 Example4-35 B-3 C-14 13.7 4.5 250 Example 4-36 B-3 C-16 14.0 4.0 225 Example4-37 B-3 C-19 13.6 4.5 233 Example 4-38 B-3 C-20 13.5 4.6 298 Example4-39 B-3 C-22 13.8 4.1 213 Example 4-40 B-4 C-11 14.7 3.6 291 Example4-41 B-4 C-12 14.7 3.8 240 Example 4-42 B-4 C-14 13.2 4.8 261 Example4-43 B-4 C-17 15.0 3.2 255 Example 4-44 B-4 C-20 13.1 5.0 319 Example4-45 B-4 C-23 15.0 3.3 259 Example 4-46 B-5 C-11 14.8 3.5 263 Example4-47 B-5 C-13 13.8 4.5 219 Example 4-48 B-5 C-14 13.5 4.9 231 Example4-49 B-5 C-18 14.3 4.0 207 Example 4-50 B-5 C-19 13.4 4.8 227 Example4-51 B-5 C-20 13.2 5.1 275 Example 4-52 B-5 C-21 14.7 3.5 229 Example4-53 B-6 C-2 14.7 3.0 298 Example 4-54 B-6 C-11 14.4 3.4 322 Example4-55 B-6 C-12 14.3 3.7 267 Example 4-56 B-6 C-14 13.3 4.5 291 Example4-57 B-6 C-16 13.8 4.1 271 Example 4-58 B-6 C-20 13.2 4.8 333 Example4-59 B-6 C-23 14.8 3.0 297 Example 4-60 B-7 C-11 14.6 3.6 286 Example4-61 B-7 C-13 13.5 4.0 227 Example 4-62 B-7 C-14 13.1 4.5 240 Example4-63 B-7 C-15 13.3 4.2 229 Example 4-64 B-7 C-19 13.2 4.6 243 Example4-65 B-7 C-20 12.9 4.7 302 Example 4-66 B-7 C-22 13.5 3.9 204 Example4-67 B-9 C-11 14.8 3.3 271 Example 4-68 B-9 C-12 14.5 3.7 208 Example4-69 B-9 C-14 13.3 4.4 235 Example 4-70 B-9 C-17 15.3 2.9 255 Example4-71 B-9 C-18 14.7 3.3 197 Example 4-72 B-9 C-20 13.1 4.8 277 Example4-73 B-9 C-23 15.4 3.0 262 Example 4-74 B-2 C-26 14.0 3.7 227 Example4-75 B-3 C-25 13.6 4.3 209 Example 4-76 B-4 C-24 14.5 3.7 263 Example4-77 B-5 C-26 14.5 3.8 220 Example 4-78 B-6 C-25 14.0 4.0 245 Example4-79 B-7 C-24 14.4 3.8 238 Example 4-80 B-9 C-25 14.2 3.9 197 Example4-81 B-2 C-29 13.2 3.8 209 Example 4-82 B-3 C-28 13.6 4.3 229 Example4-83 B-4 C-27 14.9 3.4 266 Example 4-84 B-5 C-29 14.0 4.4 211 Example4-85 B-6 C-27 14.8 3.1 293 Example 4-86 B-7 C-28 14.0 3.8 232 Example4-88 B-9 C-27 15.2 2.9 240 Example 4-89 B-2 C-30 14.7 3.0 255 Example4-90 B-2 C-32 14.6 3.0 228 Example 4-91 B-2 C-34 14.7 3.1 241 Example4-92 B-2 C-38 13.3 4.0 212 Example 4-93 B-2 C-43 13.0 4.0 210 Example4-94 B-2 C-44 14.6 3.2 242 Example 4-95 B-3 C-30 14.9 3.1 277 Example4-96 B-3 C-33 14.6 3.2 240 Example 4-97 B-3 C-34 14.8 3.1 262 Example4-98 B-3 C-35 14.5 3.5 238 Example 4-99 B-3 C-37 13.6 4.3 228 Example4-100 B-3 C-39 13.7 4.6 223 Example 4-101 B-3 C-45 14.0 4.3 239 Example4-102 B-4 C-30 14.9 3.4 299 Example 4-103 B-4 C-32 14.6 3.5 264 Example4-104 B-4 C-33 14.7 3.4 258 Example 4-105 B-4 C-40 14.8 3.3 281 Example4-106 B-4 C-41 14.3 3.9 242 Example 4-107 B-4 C-43 13.3 4.6 255 Example4-108 B-4 C-45 14.2 3.9 263 Example 4-109 B-5 C-30 14.9 3.1 273 Example4-110 B-5 C-34 14.8 3.1 259 Example 4-111 B-5 C-35 14.4 3.6 234 Example4-112 B-5 C-39 13.8 4.2 230 Example 4-113 B-5 C-42 13.8 4.3 222 Example4-114 B-5 C-44 15.0 3.3 255 Example 4-115 B-5 C-45 14.5 3.7 238 Example4-116 B-6 C-30 14.7 3.1 293 Example 4-117 B-6 C-31 14.2 3.5 272 Example4-118 B-6 C-32 14.5 3.3 266 Example 4-119 B-6 C-34 14.8 3.1 284 Example4-120 B-6 C-42 13.6 3.8 259 Example 4-121 B-6 C-43 13.3 4.3 266 Example4-122 B-6 C-45 14.2 3.8 278 Example 4-123 B-7 C-30 14.9 3.1 280 Example4-124 B-7 C-31 14.4 3.6 262 Example 4-125 B-7 C-35 14.3 3.6 249 Example4-126 B-7 C-36 13.7 4.2 222 Example 4-127 B-7 C-37 13.4 4.5 228 Example4-128 B-7 C-43 13.3 4.4 233 Example 4-129 B-7 C-45 14.1 4.0 266 Example4-130 B-9 C-30 15.1 3.0 284 Example 4-131 B-9 C-34 15.0 3.0 271 Example4-132 B-9 C-35 14.3 3.9 247 Example 4-133 B-9 C-36 14.0 4.1 225 Example4-134 B-9 C-37 13.3 4.6 235 Example 4-135 B-9 C-43 13.1 4.8 259 Example4-136 B-9 C-45 14.2 4.0 270 Example 4-137 B-2 C-46 14.2 3.4 256 Example4-138 B-2 C-48 13.7 3.8 240 Example 4-139 B-2 C-50 12.7 4.5 292 Example4-140 B-2 C-52 14.8 3.0 255 Example 4-141 B-2 C-57 14.6 3.2 269 Example4-142 B-2 C-58 14.0 3.5 243 Example 4-143 B-3 C-46 14.2 3.7 251 Example4-144 B-3 C-49 13.8 4.1 226 Example 4-145 B-3 C-50 13.5 4.6 288 Example4-146 B-3 C-51 15.0 3.1 252 Example 4-147 B-3 C-53 14.8 3.2 259 Example4-148 B-3 C-55 14.8 3.3 247 Example 4-149 B-3 C-59 14.6 3.4 233 Example4-150 B-4 C-46 14.4 3.8 271 Example 4-151 B-4 C-48 13.8 4.4 257 Example4-152 B-4 C-50 13.3 4.9 306 Example 4-153 B-4 C-52 15.0 3.3 268 Example4-154 B-4 C-54 14.5 3.7 235 Example 4-155 B-4 C-57 14.9 3.6 288 Example4-156 B-4 C-59 14.8 3.5 256 Example 4-157 B-5 C-46 14.5 3.7 257 Example4-158 B-5 C-50 13.5 4.9 280 Example 4-159 B-5 C-52 15.1 3.0 253 Example4-160 B-5 C-54 14.4 3.8 229 Example 4-161 B-5 C-56 14.0 4.3 202 Example4-162 B-5 C-58 14.1 3.9 243 Example 4-163 B-5 C-59 14.8 3.2 235 Example4-164 B-6 C-46 14.3 3.8 297 Example 4-165 B-6 C-47 14.6 3.4 267 Example4-166 B-6 C-49 13.7 4.2 255 Example 4-167 B-6 C-50 13.2 4.7 324 Example4-168 B-6 C-52 15.0 3.1 271 Example 4-169 B-6 C-54 14.0 4.0 249 Example4-170 B-6 C-59 14.7 3.3 259 Example 4-171 B-7 C-46 14.3 3.8 262 Example4-172 B-7 C-47 14.7 3.4 248 Example 4-173 B-7 C-51 15.0 3.1 264 Example4-174 B-7 C-53 14.8 3.3 272 Example 4-175 B-7 C-55 14.7 3.4 260 Example4-176 B-7 C-57 14.9 3.3 273 Example 4-177 B-7 C-58 14.0 4.0 248 Example4-178 B-9 C-46 14.6 3.7 252 Example 4-179 B-9 C-50 13.1 4.7 299 Example4-180 B-9 C-51 15.0 3.0 254 Example 4-181 B-9 C-52 14.8 3.2 255 Example4-182 B-9 C-53 14.6 3.3 243 Example 4-183 B-9 C-57 14.9 3.3 261 Example4-184 B-9 C-59 14.5 3.5 239

As apparent from the above results, the device of the present inventionhad higher external quantum efficiency and lower driving voltage thanthe comparative devices. In particular, high durability was shown whendriving at a high temperature (70° C.). Example 4 exemplifies themanufacture of a light emitting layer by coating, and is excellent interms of manufacturing costs.

Industrial Applicability

According to the present invention, an organic electroluminescencedevice having excellent light emission efficiency and durability (inparticular, durability when driving at high temperature) may beprovided.

Although the present invention has been described with reference todetailed and specific embodiments thereof, it is obvious to thoseskilled in the art that various changes or modifications may be madewithout departing from the spirit and scope of the present invention.

This application claims priority from Japanese Patent Application(Japanese Patent Application No. 2009-201153) filed on Aug. 31, 2009,Japanese Patent Application (Japanese Patent Application No.2009-223456) filed on Sep. 28, 2009, and Japanese Patent Application(Japanese Patent Application No. 2010-076449) filed on Mar. 29, 2010,the disclosures of which are incorporated herein by reference in itsentirety.

Explanation of Reference Numerals and Symbols

2: Substrate

3: Anode

4: Hole injection layer

5: Hole transporting layer

6: Light emitting layer

7: Hole blocking layer

8: Electron transporting layer

9: Cathode

10: Organic electroluminescence device (Organic EL device)

11: Organic layer

12: Protective layer

14: Adhesive layer

16: Sealing vessel

20: Light emission apparatus

30: Light scattering member

30A: Light incident surface

30B: Light reflecting surface

31: Transparent substrate

32: Microparticulate

40: Illumination apparatus

The invention claimed is:
 1. An organic electroluminescence device,comprising on a substrate: a pair of electrodes; at least one layer ofan organic layer including a light emitting layer containing a lightemitting material disposed between the electrodes, wherein the lightemitting layer contains at least each one of a compound represented bythe following Formula (3) and a compound represented by the followingFormula (D-5):Z³—(Y³)_(n 3)   (3) wherein Z³ represents benzene, or biphenyl and maybe further substituted by at least one group selected from the groupconsisting of an alkyl group, an aryl group, a silyl group, a cyanogroup, a fluorine atom and a combination thereof; Y³ represents a grouprepresented by the following Formula (15a); and n³ represents an integerof 2:

wherein R₁₅₅ represents a hydrogen atom; each of R₁₅₄ and R₁₅₆independently represents a hydrogen atom, an alkyl group, a silyl group,a fluorine atom, a cyano group or a trifluoromethyl group, and thesegroups may be further substituted with at least one of an alkyl grouphaving 1 to 6 carbon atoms and a phenyl group; R₁₅₇ represents a benzenering, a naphthalene ring, a pyridine ring, a triazine ring or apyrimidine ring, and these rings may be further substituted with atleast one group selected from a methyl group, an isobutyl group, at-butyl group, a neopentyl group, a phenyl group, a naphthyl group, acyano group and a fluorine atom; and * represents a bond for linking toZ³:

wherein each of R₃ to R₁₀ independently represents a hydrogen atom, analkyl group or an aryl group; each of R₃′ to R₆′ represents a hydrogenatom, an alkyl group or an aryl group; and each of R_(y) independentlyrepresents a hydrogen atom, an alkyl group, a perfluoroalkyl group, ahalogen atom or an aryl group; wherein the compound of formula (D-5) isselected from the group consisting of:


2. The organic electroluminescence device according to claim 1, whereinthe compound represented by Formula (3) is represented by the followingFormula (5):

wherein each of R₅₁ to R₅₆ independently represents a hydrogen atom, amethyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group, a fluorine atom or agroup represented by the following Formula (10):

wherein R₁₀₂ represents a hydrogen atom; each of R₁₀₁ and R₁₀₃independently represents a hydrogen atom, an alkyl group, a silyl group,a fluorine atom, a cyano group or a trifluoromethyl group, and thesegroups may be further substituted by at least one of an alkyl grouphaving 1 to 6carbon atoms and a phenyl group; and R₁₀₄ represents abenzene ring, a naphthalene ring, a pyridine ring, a triazine ring or apyrimidine ring, and these rings may be further substituted by at leastone group selected from the group consisting of a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom.
 3. The organicelectroluminescence device according to claim 1, wherein the compoundrepresented by Formula (3) is represented by the following Formula (6):

wherein each of R₆₁ to R₆₁₀ independently represents a hydrogen atom, amethyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group, a fluorine atom or agroup represented by the following Formula (10), provided that each ofat least two of R₆₁ to R₆₁₀ is independently a group represented by thefollowing Formula (10):

wherein R₁₀₂ represents a hydrogen atom; each of R₁₀₁ and R₁₀₃independently represents a hydrogen atom, an alkyl group, a silyl group,a fluorine atom, a cyano group or a trifluoromethyl group, and thesegroups may be further substituted by at least one of an alkyl grouphaving 1 to 6carbon atoms and a phenyl group; and R₁₀₄ represents abenzene ring, a naphthalene ring, a pyridine ring, a triazine ring or apyrimidine ring, and these rings may be further substituted by at leastone group selected from the group consisting of a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom.
 4. The organicelectroluminescence device according to claim 3, wherein the compoundrepresented by Formula (6) is represented by the following Formula (7):

wherein each of R₇₁ to R₇₈ independently represents a hydrogen atom, amethyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group, or a fluorine atom; andeach of Y₇₁ and Y₇₂ is independently a group represented by thefollowing Formula (10):

wherein R₁₀₂ represents a hydrogen atom; each of R₁₀₁ and R₁₀₃independently represents a hydrogen atom, an alkyl group, a silyl group,a fluorine atom, a cyano group or a trifluoromethyl group, and thesegroups may be further substituted by at least one of an alkyl grouphaving 1 to 6carbon atoms and a phenyl group; and R₁₀₄ represents abenzene ring, a naphthalene ring, a pyridine ring, a triazine ring or apyrimidine ring, and these rings may be further substituted by at leastone group selected from the group consisting of a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom.
 5. The organicelectroluminescence device according to claim 3, wherein the compoundrepresented by Formula (6) is represented by the following Formula (8):

wherein each of R₈₁ to R₈₈ independently represents a hydrogen atom, amethyl group, an isobutyl group, a t-butyl group, a neopentyl group, aphenyl group, a naphthyl group, a cyano group, or a fluorine atom; andeach of Y₈₁ and Y₈₂ is independently a group represented by thefollowing Formula (10):

wherein R₁₀₂ represents a hydrogen atom; each of R₁₀₁ and R₁₀₃independently represents a hydrogen atom, an alkyl group, a silyl group,a fluorine atom, a cyano group or a trifluoromethyl group, and thesegroups may be further substituted by at least one of an alkyl grouphaving 1 to 6carbon atoms and a phenyl group; and R₁₀₄ represents abenzene ring, a naphthalene ring, a pyridine ring, a triazine ring or apyrimidine ring, and these rings may be further substituted by at leastone group selected from the group consisting of a methyl group, anisobutyl group, a t-butyl group, a neopentyl group, a phenyl group, anaphthyl group, a cyano group and a fluorine atom.
 6. The organicelectroluminescence device according to claim 1, wherein the lightemitting layer containing at least each one of the compound representedby Formula (3) and the compound represented by Formula (D-5) is formedby a wet process.
 7. A light emission apparatus including the organicelectroluminescence device according to claim
 1. 8. A display apparatusincluding the organic electroluminescence device according to claim 1.9. An illumination apparatus including the organic electroluminescencedevice according to claim
 1. 10. The organic electroluminescence deviceof claim 1, wherein the compound of Formula (15a) is selected from thegroup consisting of:


11. A composition, comprising: at least each one of a compoundrepresented by the following Formula (3) and a compound represented bythe following Formula (D-5):Z³—(Y³)_(n 3)   (3) wherein Z³ represents benzene, or biphenyl, and maybe further substituted by at least one group selected from the groupconsisting of an alkyl group, an aryl group, a silyl group, a cyanogroup, a fluorine atom and a combination thereof; Y³ represents a grouprepresented by the following Formula (15a); and n³ represents an integerof 2:

wherein R₁₅₅ represents a hydrogen atom; each of R₁₅₄ and R₁₅₆independently represents a hydrogen atom, an alkyl group, a silyl group,a fluorine atom, a cyano group or a trifluoromethyl group, and thesegroups may be further substituted with at least one of an alkyl grouphaving 1 to 6 carbon atoms and a phenyl group; R₁₅₇ represents a benzenering, a naphthalene ring, a pyridine ring, a triazine ring or apyrimidine ring, and these rings may be further substituted with atleast one group selected from a methyl group, an isobutyl group, at-butyl group, a neopentyl group, a phenyl group, a naphthyl group, acyano group and a fluorine atom; and * represents a bond for linking toZ³:

wherein each of R₃ to R₁₀ independently represents a hydrogen atom, analkyl group or an aryl group; each of R₃′ to R₆′ represents a hydrogenatom, an alkyl group or an aryl group; wherein each of R_(y)independently represents a hydrogen atom, an alkyl group, aperfluoroalkyl group, a halogen atom or an aryl group; wherein thecompound of formula (D-5) is selected from the group consisting of:


12. A light emitting layer, comprising: at least each one of a compoundrepresented by the following Formula (3) and a compound represented bythe following Formula (D-5):Z³—(Y³)_(n 3)   (3) wherein Z³ represents benzene, or biphenyl and maybe further substituted by at least one group selected from the groupconsisting of an alkyl group, an aryl group, a silyl group, a cyanogroup, a fluorine atom and a combination thereof; Y³ represents a grouprepresented by the following Formula (15a); and n³ represents an integerof 2:

wherein R₁₅₅ represents a hydrogen atom; each of R₁₅₄ and R₁₅₆independently represents a hydrogen atom, an alkyl group, a silyl group,a fluorine atom, a cyano group or a trifluoromethyl group, and thesegroups may be further substituted with at least one of an alkyl grouphaving 1 to 6 carbon atoms and a phenyl group; R₁₅₇ represents a benzenering, a naphthalene ring, a pyridine ring, a triazine ring or apyrimidine ring, and these rings may be further substituted with atleast one group selected from a methyl group, an isobutyl group, at-butyl group, a neopentyl group, a phenyl group, a naphthyl group, acyano group and a fluorine atom; and represents a bond for linking toZ³:

wherein each of R₃ to R₁₀ independently represents a hydrogen atom, analkyl group or an aryl group; R₃′ to R₆′ represents a hydrogen atom, analkyl group or an aryl group; wherein each of R_(y) independentlyrepresents a hydrogen atom, an alkyl group, a perfluoroalkyl group, ahalogen atom or an aryl group wherein the compound of formula (D-5) isselected from the group consisting of: